KR101331341B1 - Triazine compounds as pi3 kinase and mtor inhibitors - Google Patents

Triazine compounds as pi3 kinase and mtor inhibitors Download PDF

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KR101331341B1
KR101331341B1 KR1020107026145A KR20107026145A KR101331341B1 KR 101331341 B1 KR101331341 B1 KR 101331341B1 KR 1020107026145 A KR1020107026145 A KR 1020107026145A KR 20107026145 A KR20107026145 A KR 20107026145A KR 101331341 B1 KR101331341 B1 KR 101331341B1
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phenyl
triazin
urea
morpholin
carbonyl
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KR20110002485A (en
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아라나파캄 엠. 벤카테산
제쳉 첸
크리스토프 엠. 덴하르트
오스발도 도스 산토스
에프렌 귈러모 델로스 산토스
아리에 자스크
제로엔 씨. 버레이젠
조슈아 아론 카프란
데이비드 제이. 리차드
세미라미스 에이랄-칼로우스티안
타렉 에스. 만수르
아리아말라 고팔사미
케빈 제이. 쿠란
멩시아오 시
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Abstract

본원에서는 하기 화학식 I의 화합물 및 그의 제약상 허용되는 염 및 에스테르를 정의한다.
<화학식 I>

Figure 112010076169004-pct00158

상기 식 중,
R1은 하기 화학식 II 또는 화학식 III이고;
<화학식 II>
Figure 112010076169004-pct00159

<화학식 III>
Figure 112010076169004-pct00160

상기 식 중, R2, R4 및 R6 -9는 본원에 정의한 바와 같다.
이들 화합물은 PI3 키나제 및 mTOR을 억제하고, PI3 키나제 및 mTOR 매개 질환, 예컨대 다양한 암의 치료에 사용될 수 있다. 본 발명의 화합물의 제조 방법 및 사용 방법이 개시되어 있다. 본 발명의 화합물을 함유한 다양한 조성물이 또한 개시되어 있다.Herein are defined compounds of formula (I) and pharmaceutically acceptable salts and esters thereof.
(I)
Figure 112010076169004-pct00158

Wherein,
R 1 is the following formula II or formula III;
<Formula II>
Figure 112010076169004-pct00159

(III)
Figure 112010076169004-pct00160

In the formula, R 2, R 4 and R 6 -9 are as defined herein.
These compounds inhibit PI3 kinase and mTOR and can be used to treat PI3 kinase and mTOR mediated diseases such as various cancers. Methods of making and using the compounds of the present invention are disclosed. Various compositions containing the compounds of the present invention are also disclosed.

Description

ＰＩ３ 키나제 및 ＭＴＯＲ 억제제로서의 트리아진 화합물 {TRIAZINE COMPOUNDS AS PI3 KINASE AND MTOR INHIBITORS}TRIAZINE COMPOUNDS AS PI3 KINASE AND MTOR INHIBITORS as PI3 Kinase and MTOR inhibitors

본 발명은 PI3 키나제 및 mTOR를 억제하는 2,4,6-치환된 [1,3,5]트리아진 화합물 (여기서, 하나의 치환기는 임의로 치환된 모르폴리노, 테트라히드로피라닐 또는 디히드로피라닐 기임), 그의 제조 방법, 그를 사용한 치료 방법, 및 그를 함유하는 제약 조성물에 관한 것이다. The present invention relates to 2,4,6-substituted [1,3,5] triazine compounds that inhibit PI3 kinase and mTOR wherein one substituent is optionally substituted morpholino, tetrahydropyranyl or dihydropyra Yl group), methods for the preparation thereof, methods of treatment using the same, and pharmaceutical compositions containing the same.

포스파티딜이노시톨 (이하에, 약어 "PI"로 표시함)은 세포 막에 있는 인지질 중 하나이다. 최근 몇 년 동안 PI가 또한 세포내 신호 전달에서 중요한 역할을 한다는 것이 명백해졌다. PI (4,5) 비스포스페이트 (PI(4,5)P2 또는 PIP2)가 포스포리파제 C에 의해 디아실글리세롤 및 이노시톨 (1,4,5) 트리포스페이트로 분해되어 각각 단백질 키나제 C의 활성화 및 세포내 칼슘 이동을 유도한다는 것이 당업계에 잘 인지되어 있다 [M. J. Berridge et al., Nature, 312, 315 (1984); Y. Nishizuka, Science, 225, 1365 (1984)]. Phosphatidylinositol (hereinafter, abbreviated as "PI") is one of the phospholipids in the cell membrane. In recent years it has become apparent that PI also plays an important role in intracellular signal transduction. PI (4,5) bisphosphate (PI (4,5) P2 or PIP2) is cleaved by phospholipase C into diacylglycerol and inositol (1,4,5) triphosphate to activate protein kinase C and It is well recognized in the art that induces intracellular calcium migration [M. J. Berridge et al., Nature, 312, 315 (1984); Y. Nishizuka, Science, 225,1365 (1984)].

포스파티딜이노시톨-3 키나제 ("PI3K")는 포스파티딜이노시톨의 이노시톨 고리의 3-위치를 인산화시키는 효소이다 [D. Whitman et al., Nature, 332, 664 (1988)]. 다수의 PI3K 아형이 존재한다. PI3K의 세가지 주요 아형은 현재 그들의 시험관내 기질 특이성을 기초하여 확인된 바 있고, 이들 세가지는 클래스 I (a & b), 클래스 II 및 클래스 III으로 지정된다 [B. Vanhaesebroeck, Trend in Biol. Sci., 22, 267(1997)]. Phosphatidyl inositol-3 kinase ("PI3K") is an enzyme that phosphorylates the 3-position of the inositol ring of phosphatidylinositol [D. Whitman et al., Nature, 332, 664 (1988). There are a number of PI3K subtypes. Three major subtypes of PI3K have now been identified based on their in vitro substrate specificity, and these three are designated as Class I (a & b), Class II and Class III [B. Vanhaesebroeck, Trend in Biol. Sci., 22, 267 (1997).

클래스 Ia PI3K 아형은 현재까지 가장 광범위하게 연구되어 왔다. 클래스 Ia 아형 내에는 촉매성 110-kDa 서브유닛 및 50-85kDa의 조절 서브유닛의 헤테로 이량체로서 존재하는 3가지 이소형 (α, β & δ)으로 존재한다. 조절 서브유닛은 SH2 도메인을 함유하고, 이는 성장 인자 수용체 또는 어댑터 분자 내 인산화 티로신 잔기에 결합하여, 이에 따라 PI3K를 내부 세포 막에 국재화시킨다. 내부 세포 막에서 PI3K는 PIP2를 PIP3 (포스파티딜이노시톨-3,4,5-트리스포스페이트)으로 전환시키며, 이것은 Akt 활성화가 발생하는 내부 세포 막에 하류 이펙터 PDK1 및 Akt를 국재화시키는 작용을 한다. 활성화된 Akt는 아폽토시스, 세포 주기 진행, 인슐린 신호전달에 대한 반응, 및 세포 증식의 억제를 비롯한 다양한 계열의 효과를 매개한다. 클래스 Ia PI3K 아형은 또한 활성화된 Ras와의 연합을 허용하여, PI3K 막 국재화를 위한 또다른 메카니즘을 제공하는 Ras 결합 도메인 (RBD)를 함유한다. 활성화된 종양원성 형태의 성장 인자 수용체 (Ras) 및 심지어 PI3K 키나제는 세포 형질전환을 생성하는 PI3K/Akt/mTOR 경로에서 신호전달을 비정상적으로 상승시키는 것으로 나타났다. PI3K/Akt/mTOR 신호전달 경로의 주요 구성성분으로서 PI3K (특히 클래스 Ia 이소형)는 암 약물 개발에서 주요 치료 표적이 된다. Class Ia PI3K subtypes have been studied extensively to date. Within the class Ia subtype are three isoforms (α, β & δ) which exist as heterodimers of the catalytic 110-kDa subunit and the 50-85 kDa regulatory subunit. The regulatory subunit contains the SH2 domain, which binds to phosphorylated tyrosine residues in growth factor receptor or adapter molecules, thus localizing PI3K to the inner cell membrane. In the inner cell membrane, PI3K converts PIP2 into PIP3 (phosphatidylinositol-3,4,5-triphosphate), which acts to localize downstream effectors PDK1 and Akt in the inner cell membrane where Akt activation occurs. Activated Akt mediates a range of effects, including apoptosis, cell cycle progression, response to insulin signaling, and inhibition of cell proliferation. Class Ia PI3K subtypes also contain Ras binding domains (RBD), which allow association with activated Ras, providing another mechanism for PI3K membrane localization. Activated oncogenic forms of growth factor receptors (Ras) and even PI3K kinases have been shown to abnormally elevate signaling in the PI3K / Akt / mTOR pathway that produces cellular transformation. As a major component of the PI3K / Akt / mTOR signaling pathway, PI3K (especially class Ia isoforms) is a major therapeutic target in cancer drug development.

클래스 I PI3K를 위한 기질은 PI, PI(4)P 및 PI(4,5)P2이고, PI(4,5)P2가 가장 바람직하다. 클래스 I PI3K는, 그들의 활성화 메커니즘 및 관련 조절 서브유닛 때문에, 2개 그룹, 즉 클래스 Ia 및 클래스 Ib로 추가로 분할된다. 클래스 Ib PI3K는 G 단백질-커플링된 수용체와의 상호작용에 의해 활성화되는 p110γ이다. p110γ 및 G 단백질-커플링된 수용체 사이의 상호작용은 110, 87 및 84 kDa의 조절 서브유닛에 의해 매개된다. Substrates for class I PI3K are PI, PI (4) P and PI (4,5) P2, with PI (4,5) P2 being most preferred. Class I PI3Ks are further divided into two groups, Class Ia and Class Ib, because of their activation mechanism and associated regulatory subunits. Class Ib PI3K is p110γ which is activated by interaction with G protein-coupled receptors. The interaction between p110γ and G protein-coupled receptors is mediated by regulatory subunits of 110, 87 and 84 kDa.

PI 및 PI(4)P는 클래스 II PI3K를 위한 공지된 기질이고; PI(4,5)P2는 이 클래스의 효소에 대한 기질이 아니다. 클래스 II PI3K는 C 말단에서 C2 도메인을 함유하는 PI3K C2α, C2β 및 C2γ 이소형을 포함하며, 이는 그들의 활성이 칼슘 이온에 의해 조절되는 것을 암시한다.PI and PI (4) P are known substrates for class II PI3Ks; PI (4,5) P2 is not a substrate for this class of enzymes. Class II PI3Ks include the PI3K C2α, C2β and C2γ isoforms containing C2 domains at the C terminus, suggesting that their activity is regulated by calcium ions.

클래스 III PI3K를 위한 기질은 단지 PI이다. 클래스 III PI3K의 활성화를 위한 메카니즘은 명확하지 않다. 각각의 아형이 활성을 조절하기 위한 그 자체의 메카니즘을 가지고 있기 때문에, 활성화 메카니즘(들)은 PI3K의 각각의 클래스에 특이적인 자극에 의존적일 수 있다. The substrate for class III PI3K is only PI. The mechanism for activation of class III PI3K is not clear. Since each subtype has its own mechanism for regulating activity, the activation mechanism (s) may be dependent on stimuli specific to each class of PI3K.

화합물 PI103 (3-(4-(4-모르폴리닐)피리도[3',2':4,5]푸로[3,2-d]피리미딘-2-일)페놀)은 각각 2, 3, 및 50-80 nM의 IC50 값으로 PI3Ka 및 PI3Kg, 및 mTOR 효소를 억제한다. 암의 인간 종양 이종이식 모델에서의 상기 화합물의 마우스 I.P. 투약은 교모세포종 (PTEN null U87MG), 전립선 (PC3), 유방 (MDA-MB-468 및 MDA-MB-435), 결장 암종 (HCT 116) 및 난소 암종 (SKOV3 및 IGROV-1)을 비롯한 다수의 인간 종양 모델에 대한 활성을 입증하였다 [Raynaud et al, Pharmacologic Characterization of a Potent Inhibitor of Class I Phosphatidylinositide 3-Kinases, Cancer Res. 2007 67: 5840-5850]. Compound PI103 (3- (4- (4-morpholinyl) pyrido [3 ', 2': 4,5] furo [3,2-d] pyrimidin-2-yl) phenol) was 2, 3, respectively. And PI3Ka and PI3Kg, and mTOR enzymes with IC 50 values of 50-80 nM. Mouse IP dosing of the compound in human tumor xenograft models of cancer includes glioblastoma (PTEN null U87MG), prostate (PC3), breast (MDA-MB-468 and MDA-MB-435), colon carcinoma (HCT 116) And activity against a number of human tumor models, including ovarian carcinoma (SKOV3 and IGROV-1) [Raynaud et al, Pharmacologic Characterization of a Potent Inhibitor of Class I Phosphatidylinositide 3-Kinases, Cancer Res. 2007 67: 5840-5850.

화합물 ZSTK474 (2-(2-디플루오로메틸벤조이미다졸-1-일)-4,6-디모르폴리노-1,3,5-트리아진)는 각각 16, 4.6, 및 >10,000 nM의 IC50 값으로 PI3Ka 및 PI3Kg를 억제하지만, mTOR 효소는 억제하지 않았다 [Dexin Kong and Takao Yamori, ZSTK474 is an ATP-competitive inhibitor of class I phosphatidylinositol 3 kinase isoforms, Cancer Science, 2007, 98:10 1638-1642]. 마우스 인간 이종이식 암 모델에서 ZSTK474의 장기 경구 투여는, 400 mg/kg의 용량으로 비-소세포 폐암 (A549), 전립선암 (PC-3) 및 결장암 (WiDr)으로부터 기원된 성장을 완전히 억제하였다 [Yaguchi et al, Antitumor Activity of ZSTK474, a New Phosphatidylinositol 3-Kinase Inhibitor, J. Natl. Cancer Inst. 98: 545-556]. Compound ZSTK474 (2- (2-difluoromethylbenzoimidazol-1-yl) -4,6-dimorpholino-1,3,5-triazine) of 16, 4.6, and> 10,000 nM, respectively IC 50 values inhibit PI3Ka and PI3Kg but not mTOR enzymes [Dexin Kong and Takao Yamori, ZSTK474 is an ATP-competitive inhibitor of class I phosphatidylinositol 3 kinase isoforms, Cancer Science, 2007, 98:10 1638-1642 ]. Long-term oral administration of ZSTK474 in a mouse human xenograft cancer model completely inhibited growth originating from non-small cell lung cancer (A549), prostate cancer (PC-3) and colon cancer (WiDr) at a dose of 400 mg / kg [ Yaguchi et al, Antitumor Activity of ZSTK474, a New Phosphatidylinositol 3-Kinase Inhibitor, J. Natl. Cancer Inst. 98: 545-556.

화합물 NVP-BEZ-235 (2-메틸-2-(4-(3-메틸-2-옥소-8-(퀴놀린-3-일)-2,3-디히드로-1H-이미다조[4,5-c]퀴놀린-1-일)페닐)프로판니트릴)는 4, 5, 및 "나노몰"의 IC50 값으로 PI3Ka 및 PI3Kg 둘다, 및 mTOR 효소를 억제한다. 암의 인간 종양 이종이식 모델에서의 시험은 전립선암 (PC-3) 및 교모세포종 (U-87) 암의 인간 종양 모델에 대한 활성을 입증하였다. 이것은 2006년 12월에 임상 시험을 시작하였다 [Verheijen, J.C. and Zask, A., Phosphatidylinositol 3-kinase (PI3K) inhibitors as anticancer drugs, Drugs Fut. 2007, 32(6): 537-547]. Compound NVP-BEZ-235 (2-methyl-2- (4- (3-methyl-2-oxo-8- (quinolin-3-yl) -2,3-dihydro-1H-imidazo [4,5 -c] quinolin-1-yl) phenyl) propanenitrile) inhibits both PI3Ka and PI3Kg, and mTOR enzymes with IC 50 values of 4, 5, and "nanomol". Testing in human tumor xenograft models of cancer demonstrated activity against human tumor models of prostate cancer (PC-3) and glioblastoma (U-87) cancers. It began clinical trials in December 2006 [Verheijen, JC and Zask, A., Phosphatidylinositol 3-kinase (PI3K) inhibitors as anticancer drugs, Drugs Fut. 2007, 32 (6): 537-547.

화합물 SF-1126 (LY-294002의 전구약물 형태, 2-(4-모르폴리닐)-8-페닐-4H-1-벤조피란-4-온임)은 "팬-PI3K 억제제"이다. 이것은 전립선, 유방, 난소, 폐, 다발성 골수종 및 뇌암의 전임상 마우스 암 모델에서 활성이다 [Verheijen, J.C. and Zask, A., Phosphatidylinositol 3-kinase (PI3K) inhibitors as anticancer drugs, Drugs Fut. 2007, 32(6): 537-547). Compound SF-1126 (prodrug form of LY-294002, which is 2- (4-morpholinyl) -8-phenyl-4H-1-benzopyran-4-one) is a "Pan-PI3K inhibitor". It is active in preclinical mouse cancer models of prostate, breast, ovary, lung, multiple myeloma and brain cancer [Verheijen, J.C. and Zask, A., Phosphatidylinositol 3-kinase (PI3K) inhibitors as anticancer drugs, Drugs Fut. 2007, 32 (6): 537-547).

α 이소형의 억제가 PI3K 억제제의 항종양 활성에 필수적이라는 것이 명백한 것으로 보일지라도, 특정 PI3K 이소형의 더 선택적인 억제제가 불필요한 생물학적 효과를 더 적게 도출할 수 있을지는 명백하지 않다. 비-PI3Kα 클래스 I 이소형 (PI3Kβ, δ 및 γ)이 세포의 종양원성 변형을 유도할 수 있는 능력을 가지며, 이는 비이소형 - 특이적 억제제가 특이적 억제제보다 개선된 치료학적 잠재력을 제공할 수 있음을 시사한다는 것이 최근에 보고되었다.Although it appears clear that inhibition of the α isotype is necessary for the antitumor activity of PI3K inhibitors, it is not clear whether more selective inhibitors of certain PI3K isotypes may elicit less unwanted biological effects. Non-PI3Kα class I isotypes (PI3Kβ, δ, and γ) have the ability to induce oncogenic modifications of cells, which allows non-isotype-specific inhibitors to provide improved therapeutic potential over specific inhibitors. It has recently been reported that there is.

다른 관련된 키나제에 대한 선택성은 또한 PI3K 억제제의 개발에 대한 중요한 고려사항이다. 불필요한 부작용을 피하기 위해 선택적인 억제제가 바람직할 수 있지만, PI3K/Akt 경로 (예를 들면, PI3Kα 및 mTOR [라파마이신의 포유동물 표적])의 다중 표적의 억제가 더 큰 효능을 도출할 수 있다는 보고가 존재한다. 지질 키나제 억제제는 비선택적 억제제가 또한 클리닉에 제기될 수 있다는 점에서 단백질 키나제 억제제와 유사할 수 있다는 것이 가능하다. Selectivity to other related kinases is also an important consideration for the development of PI3K inhibitors. While selective inhibitors may be desirable to avoid unnecessary side effects, reports that inhibition of multiple targets of the PI3K / Akt pathway (eg, PI3Kα and mTOR [mammalian target of rapamycin]) may lead to greater efficacy. Is present. It is possible that lipid kinase inhibitors can be similar to protein kinase inhibitors in that non-selective inhibitors can also be raised in clinics.

라파마이신 포유동물 표적 (mTOR)은 영양소 및 성장 인자에 대한 종양 세포의 반응, 및 혈관 내피 성장 인자 (VEGF)에 대한 영향을 통한 종양 혈액 공급의 제어를 조절하는 세포-신호전달 단백질이다. mTOR의 억제제는 mTOR의 효과를 억제함으로써 암 세포를 결핍시키고 종양을 수축시킨다. 모든 mTOR 억제제는 mTOR 키나제에 결합한다. 이것은 적어도 2가지의 중요한 효과를 갖는다. 첫째, mTOR은 PI3K/Akt 경로의 하류 매개인자이다. PI3K/Akt 경로는 다수의 암에서 과활성화되는 것으로 여겨지고, mTOR 억제제에 대한 다양한 암으로부터의 광범위한 반응을 설명할 수 있다. 또한, 상류 경로의 과활성화는 보통 mTOR 키나제가 과활성화되기 때문일 것이다. 그러나, mTOR 억제제의 존재 하에서는 상기 절차가 차단된다. 이러한 차단 효과는 세포 성장을 제어하는 하류 경로로의 신호전달로부터 mTOR을 방지한다. PI3K/Akt 키나제 경로의 과활성화는 주로 PTEN 유전자에서의 돌연변이와 관련되고, 이것은 다수의 암에서 일반적이며, 어떤 종양이 mTOR 억제제에 대해 반응할 것인지의 예측을 보조할 수 있다. mTOR 억제의 두번째 주요 효과는 VEGF 수준의 저하를 통한 항혈관신생이다.Rapamycin mammalian target (mTOR) is a cell-signaling protein that regulates the response of tumor cells to nutrients and growth factors, and the control of tumor blood supply through the effects on vascular endothelial growth factor (VEGF). Inhibitors of mTOR deplete cancer cells and constrict tumors by inhibiting the effects of mTOR. All mTOR inhibitors bind to mTOR kinases. This has at least two important effects. First, mTOR is a downstream mediator of the PI3K / Akt pathway. The PI3K / Akt pathway is believed to be overactivated in many cancers and may explain a wide range of responses from various cancers to mTOR inhibitors. In addition, overactivation of the upstream pathway will usually be due to overactivation of the mTOR kinase. However, the procedure is blocked in the presence of mTOR inhibitors. This blocking effect prevents mTOR from signaling to downstream pathways that control cell growth. Overactivation of the PI3K / Akt kinase pathway is mainly associated with mutations in the PTEN gene, which is common in many cancers and can assist in the prediction of which tumors will respond to mTOR inhibitors. The second major effect of mTOR inhibition is antiangiogenesis through lowering of VEGF levels.

실험실 시험에서, 특정 화학요법제는 mTOR 억제제의 존재 하에 더 효과적인 것으로 밝혀졌다 [George, J.N., et al., Cancer Research, 61, 1527-1532, 2001]. 추가의 실험실 결과는 일부의 횡문근육종 세포가 mTOR 억제제의 존재 하에 사멸된다는 것을 보여주었다. In laboratory tests, certain chemotherapeutic agents have been found to be more effective in the presence of mTOR inhibitors (George, J.N., et al., Cancer Research, 61, 1527-1532, 2001). Further laboratory results have shown that some rhabdomyosarcoma cells die in the presence of mTOR inhibitors.

임상 시험을 진행하고 있는 3종의 mTOR 억제제가 있다. 이들 화합물은 42-(3-히드록시-2-(히드록시메틸)-라파마이신 2-메틸프로파노에이트 (CCI-779) 또는 템시롤리무스(Temsirolimus)로서 공지된 와이어쓰(Wyeth)의 토리셀(Torisel); 42-O-(2-히드록시에틸)-라파마이신 또는 RAD 001로서도 공지된 노파르티스의 에베롤리무스(Everolimus); 및 42-(디메틸포프시노일)-라파마이신으로서도 공지된 아리아드의 AP23573이다. FDA는 진행성 신세포 암종의 치료를 위해 토리셀을 승인하였다. 게다가, 토리셀은 급성 림프모구성 백혈병의 NOS/SCID 이종이식 마우스 모델에서 활성이다 [Teachey et al, Blood, 107(3), 1149-1155, 2006]. 2009년 3월 30일에, 미국 식품의약국 (FDA)은 진행성 신세포 암종에 걸린 환자의 치료를 위해 에버롤리무스 (아피니토르(AFINITOR)™)를 승인하였다. AP23573은 연조직 및 골 육종의 치료를 위한, FDA의 희귀 의약품 및 우선 심사 대상에 해당한다. There are three mTOR inhibitors that are undergoing clinical trials. These compounds are Wyeth's tolycel known as 42- (3-hydroxy-2- (hydroxymethyl) -rapamycin 2-methylpropanoate (CCI-779) or temsirolimus. Torisel; Everolimus of Nopartis, also known as 42-O- (2-hydroxyethyl) -rapamycin or RAD 001; and also known as 42- (dimethylphosphinoyl) -rapamycin ARID, AP23573. The FDA approved toricel for the treatment of advanced renal cell carcinoma, in addition, toricel is active in NOS / SCID xenograft mouse models of acute lymphoblastic leukemia [Teachey et al, Blood, 107 (3), 1149-1155, 2006. On March 30, 2009, the U.S. Food and Drug Administration (FDA) determined Everolimus (AFINITOR ™) for the treatment of patients with advanced renal cell carcinoma. AP23573 is FDA's rare drug and priority review for the treatment of soft tissue and osteosarcoma Correspond.

3종의 mTOR 억제제는 재생가능하지만 비-선형인 약동학 프로필을 가지고 있다. 이러한 약물에 대한 곡선 아래의 평균 면적 (AUC) 값은 용량 관련 방법보다 적게 증가한다. 3종의 화합물은 모두 천연 마클로리드 항생제 라파마이신의 반-합성 유도체이다. 더 강력하고 개선된 약동학 행동을 나타내는, mTOR를 억제하는 완전 합성 화합물을 밝혀내는 것이 바람직할 것이다. Three mTOR inhibitors have a pharmacokinetic profile that is renewable but non-linear. The mean area under the curve (AUC) values for these drugs increase less than the dose related method. All three compounds are semi-synthetic derivatives of the natural maclolide antibiotic rapamycin. It would be desirable to identify fully synthetic compounds that inhibit mTOR that exhibit more potent and improved pharmacokinetic behavior.

<발명의 요약>SUMMARY OF THE INVENTION [

본 발명은 하기 화학식 I의 화합물 및 그의 제약상 허용되는 염 및 에스테르를 제공한다:The present invention provides compounds of formula I and their pharmaceutically acceptable salts and esters:

<화학식 I><Formula I>

Figure 112010076169004-pct00001
Figure 112010076169004-pct00001

상기 식 중,Wherein,

R1은

Figure 112010076169004-pct00002
이고;R 1 is
Figure 112010076169004-pct00002
ego;

R2, R4 및 R6 -9는 하기에 정의된다.R 2 , R 4 and R 6 -9 are defined below.

이들 화합물은 mTOR 및 PI3 키나제의 억제제로서 유용하다. These compounds are useful as inhibitors of mTOR and PI3 kinases.

본 발명은 추가로 하나 이상의 상술한 화합물을 함유한 조성물을 제공하고, 상기 조성물은 제약상 허용되는 담체를 함유할 수 있다. The present invention further provides compositions containing one or more of the aforementioned compounds, which compositions may contain a pharmaceutically acceptable carrier.

본 발명은 하기에 기술된 바와 같이 본 발명의 화합물의 제조 방법을 제공한다. 본 발명의 사용 방법은 또한, 예를 들면, mTOR의 억제 방법, PI3 키나제의 억제 방법, 및 다양한 형태의 암의 치료 방법을 제공한다. The present invention provides a process for the preparation of the compounds of the present invention as described below. The methods of use of the present invention also provide methods of inhibiting mTOR, methods of inhibiting PI3 kinase, and methods of treating various forms of cancer, for example.

<방법의 상세한 설명> <Detailed description of the method>

한 측면에서, 본 발명은 하기 화학식 I의 화합물 및 그의 제약상 허용되는 염 및 에스테르를 제공한다:In one aspect, the present invention provides a compound of formula (I) and pharmaceutically acceptable salts and esters thereof:

<화학식 I><Formula I>

Figure 112010076169004-pct00003
Figure 112010076169004-pct00003

상기 식 중,Wherein,

R1은

Figure 112010076169004-pct00004
이고;R 1 is
Figure 112010076169004-pct00004
ego;

여기서,here,

R6, R7, R8, R9는 각각 독립적으로 수소 원자, 및 C2-C6알케닐, C4-C6알카디에닐, C2-C6알키닐 또는 C4-C6알카디이닐로 임의로 치환된 C1-C6알킬로 이루어진 군으로부터 선택되거나;R 6 , R 7 , R 8 , R 9 are each independently a hydrogen atom and C 2 -C 6 alkenyl, C 4 -C 6 alkadienyl, C 2 -C 6 alkynyl or C 4 -C 6 alkadiyi C 1 -C 6 alkyl optionally substituted with niyl;

또는 R6 및 R7 또는 R8 및 R9 중 하나는, 이들이 부착된 탄소 원자와 함께, O, NH 및 S로부터 독립적으로 선택된 0, 1 또는 2개의 원자를 함유하는 임의로 치환된 5 내지 8원 포화 또는 불포화 고리를 형성하고;Or one of R 6 and R 7 or R 8 and R 9 , together with the carbon atoms to which they are attached, contains an optionally substituted 5 to 8 membered 0, 1 or 2 atoms independently selected from O, NH and S To form a saturated or unsaturated ring;

점선

Figure 112010076169004-pct00005
은 임의의 제2 결합을 나타내고;dotted line
Figure 112010076169004-pct00005
Represents any second bond;

R2는 임의로 치환된 C6-C14아릴-NH-COR3, 임의로 치환된 C1-C9헤테로아릴-NH-COR3, -CH=CH-C6-C10아릴-NH-COR3 또는 -CH=CH-C1-C9헤테로아릴-NH-COR3이고;R 2 is optionally substituted C 6 -C 14 aryl-NH-COR 3 , optionally substituted C 1 -C 9 heteroaryl-NH-COR 3 , -CH = CH-C 6 -C 10 aryl-NH-COR 3 or -CH = CH-C 1 -C 9 heteroaryl and -NH-COR 3;

R3은 OR5, NR5R5 또는 NHR5이고;R 3 is OR 5 , NR 5 R 5 or NHR 5 ;

R5는 독립적으로 C1-C6알킬, C3-C6알케닐, C3-C6알키닐, 임의로 치환된 C6-C10아릴, C1-C6할로알킬, 임의로 치환된 C1-C9헤테로아릴, C1-C6히드록시알킬-, 및 OH, NR11R11 또는 3원 내지 7원 C1-C6헤테로시클릴로 임의로 치환된 C3-C10 포화 또는 불포화 모노 또는 비시클릭 C3-C10시클로알킬, 및 3원 내지 10원 포화 또는 불포화 모노 또는 비시클릭 C1-C9헤테로시클릴로 이루어진 군으로부터 선택되되, 단, 3원 시클로알킬 및 헤테로시클릴 고리는 포화된 것이거나;R 5 is independently C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, optionally substituted C 6 -C 10 aryl, C 1 -C 6 haloalkyl, optionally substituted C C 3 -C 10 saturated or unsaturated mono optionally substituted with 1- C 9 heteroaryl, C 1 -C 6 hydroxyalkyl-, and OH, NR 11 R 11 or 3- to 7-membered C 1 -C 6 heterocyclyl Or bicyclic C 3 -C 10 cycloalkyl, and 3 to 10 membered saturated or unsaturated mono or bicyclic C 1 -C 9 heterocyclyl, provided that the 3 membered cycloalkyl and heterocyclyl ring is Saturated;

또는 2개의 R5 기는, 이들이 부착되어 있는 질소 원자와 함께, C1-C6알킬로 임의로 치환된 3원 내지 8원 고리계를 형성하고, 여기서 상기 고리계는 포화 또는 불포화된 것이고, 상기 질소 원자 이외에, O, S, S(O), S(O)2 및 NR10으로부터 선택된 0 내지 2개의 헤테로원자 고리원을 갖고;Or two R 5 groups together with the nitrogen atom to which they are attached form a three to eight membered ring system optionally substituted with C 1 -C 6 alkyl, wherein the ring system is saturated or unsaturated, and the nitrogen In addition to an atom, it has 0 to 2 heteroatomic ring members selected from O, S, S (O), S (O) 2 and NR 10 ;

R10은 H, C1-C6알킬, -SO2(C1-C6알킬), -COO(C1-C6알킬), -CONH(C1-C6알킬), -CON(C1-C6알킬)2, -CO(C1-C6알킬) 및 -SO2NHR11로 이루어진 군으로부터 선택되고;R 10 is H, C 1 -C 6 alkyl, -SO 2 (C 1 -C 6 alkyl), -COO (C 1 -C 6 alkyl), -CONH (C 1 -C 6 alkyl), -CON (C 1 -C 6 alkyl) 2 , -CO (C 1 -C 6 alkyl) and -SO 2 NHR 11 ;

R11은 H, 및 OH, NR11R11 또는 3원 내지 7원 C1-C6헤테로시클릴로 임의로 치환된 C1-C6알킬, -CO(C1-C6알킬), 임의로 치환된 C6-C10아릴, 및 임의로 치환된 C1-C9헤테로아릴로 이루어진 군으로부터 선택되고;R 11 is H, and C 1 -C 6 alkyl optionally substituted with OH, NR 11 R 11 or 3- to 7-membered C 1 -C 6 heterocyclyl, —CO (C 1 -C 6 alkyl), optionally substituted C 6 -C 10 aryl, and optionally substituted C 1 -C 9 heteroaryl;

R4는 a) i) C1-C6알킬-로 임의로 치환된 3원 내지 10원 C1-C9헤테로시클릴, ii) H2N-, iii) (C1-C6알킬)NH-, iv) (C1-C6알킬)2N-, v) NH(CH2)aN(C1-C6알킬)2 (여기서, a는 2, 3 또는 4임) 및 vi) CHO로 임의로 치환된 C1-C6알킬; b) C3-C6알케닐; c) C3-C6알키닐; d) -O-C1-C8알킬로 임의로 치환된 -O-C1-C8알킬; e) -O-C3-C8알케닐; f) -O-C3-C8알키닐; g) 포화 또는 불포화 모노 또는 비시클릭 C3-C8시클로알킬; 및 h) 포화 또는 불포화 모노 또는 비시클릭 -O-C3-C12시클로알킬 (이들 모두는 OH, NR11R11, 또는 C1-C6알킬-로 임의로 치환된 3원 내지 7원 C1-C6헤테로시클릴로 임의로 치환되고, 단, OH 또는 NR11R11은 또다른 탄소 원자에 대해 이중-결합 또는 삼중-결합된 탄소 원자에 직접 결합되지는 않음); i) -CH=CH-C6-C10아릴; j) -CH=CH-C1-C9헤테로아릴; k) 임의로 치환된 C6-C10아릴; l) 탄소 원자를 통해 트리아진 잔기에 부착된, 임의로 치환된 5원 내지 10원 C1-C9헤테로아릴; m) 탄소 또는 질소 원자를 통해 트리아진 잔기에 부착되고, OH, NR11R11, C1-C6알킬, (C1-C6알킬)아미도-, (C1-C6알킬)C(O)-, (C1-C6알콕시)카르보닐-, 아다만틸, C1-C6히드록실알킬-, (C1-C6알킬)아미도-, 또는 3원 내지 7원 C1-C6헤테로시클릴로부터 독립적으로 선택되는 1 내지 3개의 치환기로 임의로 치환된 3원 내지 10원 포화 또는 불포화 모노시클릭 C1-C9헤테로시클릴 (단, 3원 헤테로시클릴은 포화된 것이고, 질소 원자를 통해 트리아진 잔기에 부착되며, 5원 비시클릭 헤테로시클릴은 포화된 것임); n) 임의로 치환된 -O-C6-C10아릴; o) 임의로 치환된 -O-C1-C9헤테로아릴; p) (C1-C6알콕시)카르보닐-, H2NS(O)2-, 또는 OH, NR11R11 또는 3원 내지 7원 C1-C6헤테로시클릴로 임의로 더 치환된 C1-C6알킬로 임의로 치환된 -O-(3원 내지 12원 포화 또는 불포화 모노 또는 비시클릭)C1-C9헤테로시클릴 (단, 3원 헤테로시클릴은 포화된 것임); q) -NHC6-C10아릴; r) -NHC1-C9헤테로아릴; s) -NHNH2; t) -NHNHC1-C6알킬; u) -NHN(C1-C6알킬)2; v) -NHOH; w) -COOH; x) -COO-C1-C6알킬; y) -CONR12R13; z) -NR12R13;R 4 is a) i) 3- to 10-membered C 1 -C 9 heterocyclyl optionally substituted with C 1 -C 6 alkyl-, ii) H 2 N-, iii) (C 1 -C 6 alkyl) NH -, iv) (C 1 -C 6 alkyl) 2 N-, v) NH (CH 2 ) a N (C 1 -C 6 alkyl) 2 , wherein a is 2, 3 or 4 and vi) CHO C 1 -C 6 alkyl optionally substituted with; b) C 3 -C 6 alkenyl; c) C 3 -C 6 alkynyl; d) -OC 1 -C 8 alkyl optionally substituted with -OC 1 -C 8 alkyl; e) -OC 3 -C 8 alkenyl; f) -OC 3 -C 8 alkynyl; g) saturated or unsaturated mono or bicyclic C 3 -C 8 cycloalkyl; And h) 3- to 7-membered C 1 -C optionally substituted with saturated or unsaturated mono or bicyclic -OC 3 -C 12 cycloalkyl, all of which are optionally substituted with OH, NR 11 R 11 , or C 1 -C 6 alkyl- Optionally substituted with 6 heterocyclyl, provided that OH or NR 11 R 11 is not directly bonded to a double- or triple-bonded carbon atom for another carbon atom; i) -CH = CH-C 6 -C 10 aryl; j) -CH = CH-C 1 -C 9 heteroaryl; k) optionally substituted C 6 -C 10 aryl; l) an optionally substituted 5-10 membered C 1 -C 9 heteroaryl attached to the triazine residue via a carbon atom; m) attached to a triazine moiety via a carbon or nitrogen atom, OH, NR 11 R 11 , C 1 -C 6 alkyl, (C 1 -C 6 alkyl) amido-, (C 1 -C 6 alkyl) C (O)-, (C 1 -C 6 alkoxy) carbonyl-, adamantyl, C 1 -C 6 hydroxylalkyl-, (C 1 -C 6 alkyl) amido-, or 3- to 7-membered C 3- to 10-membered saturated or unsaturated monocyclic C 1 -C 9 heterocyclyl optionally substituted with 1 to 3 substituents independently selected from 1- C 6 heterocyclyl, provided that 3-membered heterocyclyl is saturated Attached to the triazine moiety via a nitrogen atom and the 5-membered bicyclic heterocyclyl is saturated); n) optionally substituted -OC 6 -C 10 aryl; o) optionally substituted -OC 1 -C 9 heteroaryl; p) (C 1 -C 6 alkoxy) carbonyl -, H 2 NS (O) 2 -, or OH, NR 11 R 11 or a 3-to 7-membered C 1 -C 6 heterocycle optionally further substituted by C 1 Lilo -O- (3- to 12-membered saturated or unsaturated mono or bicyclic) C 1 -C 9 heterocyclyl optionally substituted with -C 6 alkyl, provided that the 3-membered heterocyclyl is saturated; q) -NHC 6 -C 10 aryl; r) -NHC 1 -C 9 heteroaryl; s) -NHNH 2 ; t) -NHNHC 1 -C 6 alkyl; u) -NHN (C 1 -C 6 alkyl) 2 ; v) -NHOH; w) -COOH; x) -COO-C 1 -C 6 alkyl; y) -CONR 12 R 13 ; z) -NR 12 R 13 ;

Figure 112010076169004-pct00006
Figure 112010076169004-pct00006

(여기서, Z는 CH2, O, S(O)n 또는 NR10이고, n은 0, 1 또는 2임); ee) 할로겐; ff) C6-C14아릴-S(O)2-NH-; gg) R11NHC(O)NH-O- 및 hh) 질소 원자를 통해 트리아진 잔기에 부착된, 임의로 치환된 5원 모노시클릭 C1-C4헤테로아릴로 이루어진 군으로부터 선택되고;Wherein Z is CH 2 , O, S (O) n or NR 10 and n is 0, 1 or 2; ee) halogen; ff) C 6 -C 14 aryl-S (O) 2 -NH-; gg) R 11 NHC (O) NH-O- and hh) an optionally substituted 5-membered monocyclic C 1 -C 4 heteroaryl attached to a triazine residue via a nitrogen atom;

R12 및 R13은 각각 독립적으로 H, 임의로 일치환 또는 이치환된 C1-C8알킬, 임의로 치환된 C3-C8알케닐, 및 임의로 치환된 C3-C8알키닐로부터 선택되거나 (임의의 치환기는 C1-C6알콕시, OH, NR11R11 및 3원 내지 7원 C1-C6헤테로시클릴로부터 선택되되, 단, OH 또는 NR11R11은 또다른 탄소 원자에 이중-결합 또는 삼중-결합된 탄소 원자에 직접 결합되지는 않음);R 12 and R 13 are each independently selected from H, optionally mono- or di-substituted C 1 -C 8 alkyl, optionally substituted C 3 -C 8 alkenyl, and optionally substituted C 3 -C 8 alkynyl ( Optional substituents are selected from C 1 -C 6 alkoxy, OH, NR 11 R 11 and 3- to 7-membered C 1 -C 6 heterocyclyl, provided that OH or NR 11 R 11 is substituted at another carbon atom Not directly bonded to a bonded or triple-bonded carbon atom);

또는 R12 및 R13은, 이들이 부착되어 있는 질소 원자와 함께, C1-C6알킬로 임의로 치환된 3원 내지 8원 모노시클릭 고리계를 형성하거나 (여기서, 상기 고리계는 포화 또는 불포화된 것이고, 상기 질소 원자 이외에, O, S(O)n 및 NR10으로부터 선택된 0 내지 2개의 헤테로원자 고리원을 가짐);Or R 12 and R 13 together with the nitrogen atom to which they are attached form a 3- to 8-membered monocyclic ring system optionally substituted with C 1 -C 6 alkyl, wherein the ring system is saturated or unsaturated Having 0 to 2 heteroatom ring members selected from O, S (O) n and NR 10 in addition to the nitrogen atom;

또는 R12 및 R13은, 이들이 부착되어 있는 질소 원자와 함께,Or R 12 and R 13 together with the nitrogen atom to which they are attached,

Figure 112010076169004-pct00007
Figure 112010076169004-pct00007

(여기서, a 및 b는 각각 독립적으로 -CH2-, O, S 또는 NR10이고, x는 1 내지 3임)를 형성하고;Wherein a and b are each independently —CH 2 —, O, S or NR 10 and x is 1 to 3;

C1-C9헤테로아릴은 하나 이상의 고리, 및 O, NR10 및 S(O)n으로부터 독립적으로 선택된 1, 2, 3 또는 4개의 고리원을 갖는 5원 내지 10원 방향족 고리계를 지칭하고;C 1 -C 9 heteroaryl refers to a 5-10 membered aromatic ring system having at least one ring and 1, 2, 3 or 4 ring members independently selected from O, NR 10 and S (O) n and ;

C1-C9헤테로시클릴은 하나 이상의 고리, 및 O, NR10 및 S(O)n으로부터 독립적으로 선택된 1, 2, 3 또는 4개의 고리원을 갖는 3원 내지 10원 고리계를 지칭하고; C 1 -C 9 heterocyclyl refers to a 3-10 membered ring system having at least one ring and 1, 2, 3 or 4 ring members independently selected from O, NR 10 and S (O) n and ;

임의로 치환된 아릴기 및 헤테로아릴기는 비치환되거나, 또는 a) OH, NH2, NH(C1-C6알킬), N(C1-C6알킬)2, -NH(CH2)wN(C1-C6알킬)2 (여기서, w는 2, 3 또는 4임), 또는 C1-C6알킬- 치환기로부터 독립적으로 선택된 1 내지 3개로 임의로 치환된 3원 내지 10원 C1-C9헤테로시클릴로 임의로 치환된 C1-C6알킬; b) 할로겐; c) 히드록시; d) NH2; e) NO2; f) SO2NH2; g) COOH; h) COO(C1-C6알킬); i) NHCOO(C1-C6알킬); j) NH(C1-C6알킬); k) N(C1-C6알킬)2; l) C(O)NRaRb (여기서, Ra는 H 또는 C1-C6알킬이고, Rb는 H, C1-C6알킬, (C6-C14아릴)알킬- 또는 (C1-C9헤테로아릴)알킬-임); m) -Y-Q (여기서, Y는 i) O, ii) NH, iii) N(C1-C6알킬), iv) NHSO2, v) SO2NH, vi) NHCONH, vii) NHCON(C1-C6알킬), viii) S(O)q (q는 0, 1 또는 2임), ix) -C(O)NH-, x) -NHC(O)-, xi) -C(O)N(CH3)-, xii) C(O)이거나 또는 xiii) 존재하지 않고, Q는 i) A) 1) H2N-, 2) (C1-C6알킬)아미노-, 3) 디(C1-C6알킬)아미노-, 4) C1-C6알킬-에 의해 임의로 치환된 C1-C9헤테로시클릴- 또는 5) 히드록실로 치환된 임의로 치환된 C1-C6알콕시-, B) (C1-C6알콕시)카르보닐-, C) (C1-C6알콕시)C(O)NH-, D) 1) H2N-, 2) (C1-C6알킬)아미노- 또는 3) 디(C1-C6알킬)아미노-로 임의로 치환된 C1-C6알킬-, E) (C1-C6알킬)아미노-, F) 디(C1-C6알킬)아미노-, G) 1) H2N-, 2) (C1-C6알킬)아미노- 또는 3) 디(C1-C6알킬)아미노-로 임의로 치환된 (C1-C6알킬)아미도-, H) (C1-C6알킬)카르복시아미도-, I) C1-C6알킬- 또는 C1-C6히드록실알킬-로 임의로 치환된 C1-C9헤테로시클릴-, J) C1-C6알킬-로 임의로 치환된 헤테로시클릴(C1-C6알킬)-, K) 할로겐, L) 히드록실, M) C1-C6히드록실알킬-, N) 퍼플루오로(C1-C6)알킬-, O) H2N-, P) O2N-, Q) H2NSO2-, R) HO2C- 및 S) NC-로부터 독립적으로 선택된 1 내지 3개의 치환기로 임의로 치환된 C6-C10아릴, ii) A) 1) H2N-, 2) (C1-C6알킬)아미노-, 3) 디(C1-C6알킬)아미노-, 4) C1-C6알킬-로 임의로 치환된 C1-C9헤테로시클릴- 또는 5) 히드록실로 임의로 치환된 C1-C6알콕시-, B) (C1-C6알콕시)카르보닐-, C) (C1-C6알콕시)C(O)NH-, D) 1) H2N-, 2) (C1-C6알킬)아미노- 또는 3) 디(C1-C6알킬)아미노-로 임의로 치환된 C1-C6알킬-, E) (C1-C6알킬)아미노-, F) 디(C1-C6알킬)아미노-, G) 1) H2N-, 2) (C1-C6알킬)아미노- 또는 3) 디(C1-C6알킬)아미노-로 임의로 치환된 (C1-C6알킬)아미도-, H) (C1-C6알킬)카르복시아미도-, I) C1-C6알킬- 또는 C1-C6히드록실알킬-로 임의로 치환된 C1-C9헤테로시클릴-, J) C1-C6알킬-로 임의로 치환된 헤테로시클릴(C1-C6알킬)-, K) 할로겐, L) 히드록실, M) C1-C6히드록실알킬-, N) 퍼플루오로(C1-C6)알킬-, O) H2N-, P) O2N-, Q) H2NSO2-, R) HO2C- 및 S) NC-로부터 독립적으로 선택된 1 내지 3개의 치환기로 임의로 치환된 5원 내지 10원 C1-C9헤테로아릴, iii) A) C1-C6알킬-, B) 헤테로시클릴(C1-C6알킬)-, C) (C6-C14아릴)알킬-, D) C1-C8아실-, E) (C1-C6알콕시)카르보닐-, F) (C1-C6알킬)카르복실-, G) 할로겐, H) C1-C6할로알킬-, I) 히드록실, J) C1-C6히드록시알킬-, K) H2N-, L) (C1-C6알킬)아미노-, M) 디(C1-C6알킬)아미노-, N) HO2C-, O) (C1-C6알콕시)카르보닐-, P) (C1-C6알킬)카르복실-, Q) (C1-C6알킬)아미도-, R) H2NC(O)-, S) (C1-C6알킬)카르복시아미도-, T) 5원 내지 10원 C1-C9헤테로아릴, U) C6-C14아릴, V) C3-C8시클로알킬, W) 3원 내지 10원 C1-C9헤테로시클릴, X) NC- 및 Y) -NO2로부터 독립적으로 선택된 1 내지 3개의 치환기로 임의로 치환된 3원 내지 10원 C1-C9헤테로시클릴, iv) C3-C10시클로알킬, v) C1-C6알킬, vi) C2-C6알케닐, vii) C2-C6알키닐, viii) C1-C6히드록시알킬-, ix) (CH2)vO(C1-C6알킬), x) (CH2)vNH2, xi) (CH2)vNH(C1-C6알킬), xii) (CH2)vN(C1-C6알킬)2, xiii) O(CH2)vN(C1-C6알킬)2, xiv) (CH2)vC6-C10아릴, xv) -CN, xvi) (CH2)v 5원 내지 10원 C1-C9헤테로아릴, xvii) C1-C6알킬-로 임의로 치환된 (CH2)v 3원 내지 10원 C1-C9헤테로시클릴 (여기서, v는 1, 2, 3 또는 4임) 및 xviii) C1-C6퍼플루오로알킬-로부터 선택됨); 및 n) C(O)Rc (여기서, Rc는 i) H, ii) C1-C6알킬 또는 iii) C3-C6시클로알킬임)로 이루어진 군으로부터 선택된 1 또는 2개의 잔기로 치환된다.Optionally substituted aryl and heteroaryl groups are unsubstituted or a) OH, NH 2 , NH (C 1 -C 6 alkyl), N (C 1 -C 6 alkyl) 2 , -NH (CH 2 ) w N (C 1 -C 6 alkyl) 2 , wherein w is 2, 3 or 4, or a 3 to 10 membered C 1 -optionally substituted with 1 to 3 independently selected from C 1 -C 6 alkyl- substituents. C 1 -C 6 alkyl optionally substituted with C 9 heterocyclyl; b) halogen; c) hydroxy; d) NH 2 ; e) NO 2 ; f) SO 2 NH 2 ; g) COOH; h) COO (C 1 -C 6 alkyl); i) NHCOO (C 1 -C 6 alkyl); j) NH (C 1 -C 6 alkyl); k) N (C 1 -C 6 alkyl) 2 ; l) C (O) NR a R b where R a is H or C 1 -C 6 alkyl, R b is H, C 1 -C 6 alkyl, (C 6 -C 14 aryl) alkyl- or ( C 1 -C 9 heteroaryl) alkyl-; m) -YQ, where Y is i) O, ii) NH, iii) N (C 1 -C 6 alkyl), iv) NHSO 2 , v) SO 2 NH, vi) NHCONH, vii) NHCON (C 1 -C 6 alkyl), viii) S (O) q (q is 0, 1 or 2), ix) -C (O) NH-, x) -NHC (O)-, xi) -C (O) N (CH 3 )-, xii) C (O) or xiii) absent, Q is i) A) 1) H 2 N-, 2) (C 1 -C 6 alkyl) amino-, 3) di (C 1 -C 6 alkyl) amino-a by optionally substituted C 1 -C 9 heterocyclyl, - -, 4) C 1 -C 6 alkyl, or 5) hydroxyl chamber optionally a C 1 -C 6 substituted lock Alkoxy-, B) (C 1 -C 6 alkoxy) carbonyl-, C) (C 1 -C 6 alkoxy) C (O) NH-, D) 1) H 2 N-, 2) (C 1 -C 6 alkyl) amino- or 3) C 1 -C 6 alkyl-, E) (C 1 -C 6 alkyl) amino-, F) di (C 1 optionally substituted with di (C 1 -C 6 alkyl) amino- -C 6 alkyl) amino-, G) 1) H 2 N-, 2) (C 1 -C 6 alkyl) amino- or 3) (C 1 -C 6 alkyl) amino- optionally substituted with (C 1 -C 6 alkyl) amido-, H) (C 1 -C 6 alkyl) carboxamido-, I) C 1 -C 6 alkyl- or C 1 -C 6 hydroxide Hydroxyl alkyl-optionally substituted with C 1 -C 9 heterocyclyl as-optionally substituted heterocyclyl by (C 1 -C 6 alkyl) - -, J) C 1 -C 6 alkyl, K) halogen, L) hydroxyl Hydroxyl, M) C 1 -C 6 hydroxylalkyl-, N) perfluoro (C 1 -C 6 ) alkyl-, O) H 2 N-, P) O 2 N-, Q) H 2 NSO 2- , R) C 6 -C 10 aryl optionally substituted with 1 to 3 substituents independently selected from HO 2 C- and S) NC-, ii) A) 1) H 2 N-, 2) (C 1 -C 6-alkyl) amino-, 3) di (C 1 -C 6 alkyl) amino-a with an optionally substituted C 1 -C 9 heterocyclyl, - -, 4) C 1 -C 6 alkyl, 5) an optionally substituted hydroxyl chamber C 1 -C 6 alkoxy-, B) (C 1 -C 6 alkoxy) carbonyl-, C) (C 1 -C 6 alkoxy) C (O) NH-, D) 1) H 2 N-, 2 ) (C 1 -C 6 alkyl) amino- or 3) C 1 -C 6 alkyl-, E) (C 1 -C 6 alkyl) amino-, optionally substituted with di (C 1 -C 6 alkyl) amino-, F) di (C 1 -C 6 alkyl) amino-, G) 1) H 2 N-, 2) (C 1 -C 6 alkyl) amino- or 3) di (C 1 -C 6 alkyl) amino- Randomly Optionally substituted (C 1 -C 6 alkyl) amido-, H) (C 1 -C 6 alkyl) carboxamido-, I) C 1 -C 6 alkyl- or C 1 -C 6 hydroxylalkyl- substituted C 1 -C 9 heterocyclyl, -, J) C 1 -C 6 alkyl- optionally substituted heterocyclyl by (C 1 -C 6 alkyl) -, K) halogen, L) hydroxyl, M) C 1 -C 6 hydroxylalkyl-, N) perfluoro (C 1 -C 6 ) alkyl-, O) H 2 N-, P) O 2 N-, Q) H 2 NSO 2- , R) HO 2 5-10 membered C 1 -C 9 heteroaryl optionally substituted with 1 to 3 substituents independently selected from C- and S) NC-, iii) A) C 1 -C 6 alkyl-, B) heterocyclyl (C 1 -C 6 alkyl)-, C) (C 6 -C 14 aryl) alkyl-, D) C 1 -C 8 acyl-, E) (C 1 -C 6 alkoxy) carbonyl-, F) ( C 1 -C 6 alkyl) carboxyl-, G) halogen, H) C 1 -C 6 haloalkyl-, I) hydroxyl, J) C 1 -C 6 hydroxyalkyl-, K) H 2 N-, L) (C 1 -C 6 alkyl) amino-, M) di (C 1 -C 6 alkyl) amino-, N) HO 2 C-, O) (C 1 -C 6 alkoxy) carbonyl-, P) (C 1 -C 6 alkyl) carr Carboxyl-, Q) (C 1 -C 6 alkyl) amido-, R) H 2 NC (O)-, S) (C 1 -C 6 alkyl) carboxamido-, T) 5-10 member C 1- C 9 heteroaryl, U) C 6 -C 14 aryl, V) C 3 -C 8 cycloalkyl, W) 3- to 10-membered C 1 -C 9 heterocyclyl, X) NC- and Y)- 3- to 10-membered C 1 -C 9 heterocyclyl optionally substituted with 1 to 3 substituents independently selected from NO 2 , iv) C 3 -C 10 cycloalkyl, v) C 1 -C 6 alkyl, vi) C 2 -C 6 alkenyl, vii) C 2 -C 6 alkynyl, viii) C 1 -C 6 hydroxyalkyl-, ix) (CH 2 ) v O (C 1 -C 6 alkyl), x) ( CH 2 ) v NH 2 , xi) (CH 2 ) v NH (C 1 -C 6 alkyl), xii) (CH 2 ) v N (C 1 -C 6 alkyl) 2 , xiii) O (CH 2 ) v N (C 1 -C 6 alkyl) 2 , xiv) (CH 2 ) v C 6 -C 10 aryl, xv) -CN, xvi) (CH 2 ) v 5-10 membered C 1 -C 9 heteroaryl, xvii) (CH 2 ) v 3- to 10-membered C 1 -C 9 heterocyclyl optionally substituted with C 1 -C 6 alkyl-, where v is 1, 2, 3 or 4 and xviii) C 1 a -C 6 perfluoroalkyl-line from Search); And n) C (O) R c , wherein R c is i) H, ii) C 1 -C 6 alkyl or iii) C 3 -C 6 cycloalkyl Is substituted.

본 발명의 일부 실시양태에서, R1 및/또는 R4는

Figure 112010076169004-pct00008
이다.In some embodiments of the invention, R 1 and / or R 4 is
Figure 112010076169004-pct00008
to be.

일부 실시양태에서, R1 및/또는 R4는

Figure 112010076169004-pct00009
이다.In some embodiments, R 1 and / or R 4 are
Figure 112010076169004-pct00009
to be.

일부 실시양태에서, R1 또는 R4 중 하나는

Figure 112010076169004-pct00010
이고, 다른 하나는
Figure 112010076169004-pct00011
이다.In some embodiments, one of R 1 or R 4 is
Figure 112010076169004-pct00010
The other is
Figure 112010076169004-pct00011
to be.

일부 실시양태에서, R2는 임의로 치환된 C6-C14아릴-NH-COR3이고; 다른 실시양태에서 R2는 임의로 치환된 페닐-NH-COR3이다. In some embodiments, R 2 is optionally substituted C 6 -C 14 aryl-NH-COR 3 ; In other embodiments R 2 is optionally substituted phenyl-NH-COR 3 .

일부 실시양태에서, R3은 NHR5 또는 OR5이다. 일부 실시양태에서, R5는 임의로 치환된 C6-C10아릴, 예컨대 임의로 치환된 페닐 또는 C1-C9헤테로아릴이다. 일부 실시양태에서, 임의로 치환된 C6-C10아릴 또는 페닐은 -Y-Q, C(O)NRaRb 또는 C(O)Rc로 치환된다.In some embodiments, R 3 is NHR 5 or OR 5 . In some embodiments, R 5 is optionally substituted C 6 -C 10 aryl, such as optionally substituted phenyl or C 1 -C 9 heteroaryl. In some embodiments, optionally substituted C 6 -C 10 aryl or phenyl is substituted with —YQ, C (O) NR a R b or C (O) R c .

일부 실시양태에서, R5는 -Y-Q로 치환된 페닐이다. In some embodiments, R 5 is phenyl substituted with -YQ.

하기 화합물은 화학식 I의 예시된 화합물을 예증한다:The following compounds illustrate the exemplified compounds of formula I:

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-3-일우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-3-ylurea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-페닐우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-phenylurea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-티오펜-2-일우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-thiophen-2-ylurea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-메틸페닐)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-methylphenyl) urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-플루오로페닐)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-fluorophenyl) urea;

1-(2,4-디메톡시페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-우레아;1- (2,4-dimethoxyphenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -urea;

1-(4-클로로페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-chlorophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-메톡시페닐)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-methoxyphenyl) urea;

(4-클로로페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아; (4-chlorophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea;

(2,4-디플루오로페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아; (2,4-difluorophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-에틸우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-ethylurea;

tert-부틸 3-{[4-(4-{[(4-플루오로페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트;tert-butyl 3-{[4- (4-{[(4-fluorophenyl) carbamoyl] amino} phenyl) -6-morpholin-4-yl-1,3,5-triazine-2- General] amino} azetidine-1-carboxylate;

tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(페닐카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트;tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(phenylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) amino] azetidine -1-carboxylate;

tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-3-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트;tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-3-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) Amino] azetidine-1-carboxylate;

tert-부틸 3-{[4-(4-{[(4-메틸페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트;tert-butyl 3-{[4- (4-{[(4-methylphenyl) carbamoyl] amino} phenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Amino} azetidine-1-carboxylate;

1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-페닐우레아;1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-phenylurea;

1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-3-yl Urea;

1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-플루오로페닐)우레아;1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-fluoro Phenyl) urea;

1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-메틸페닐)우레아;1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-methylphenyl) Urea;

tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트;tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) Amino] azetidine-1-carboxylate;

1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-yl Urea;

1-[2-(디메틸아미노)에틸]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- [2- (dimethylamino) ethyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(2-메틸피리딘-4-일)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (2-methylpyridin-4-yl) urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(2-히드록시에틸)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (2-hydroxyethyl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-히드록시페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4-hydroxyphenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(1-히드록시에틸)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (1-hydroxyethyl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(트리플루오로메틸)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (trifluoromethyl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-히드록시페닐)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-hydroxyphenyl) urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[5-(트리플루오로메틸)피리딘-2-일]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [5- (trifluoromethyl) pyridin-2-yl ] Urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[2,2,2-트리플루오로-1-히드록시-1-(트리플루오로메틸)에틸]페닐}우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4- [2,2,2-trifluoro- 1-hydroxy-1- (trifluoromethyl) ethyl] phenyl} urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[3-(1-히드록시에틸)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [3- (1-hydroxyethyl) phenyl] urea;

메틸 4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;Methyl 4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;

1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-pyridine -4-ylurea;

1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-페닐우레아;1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-phenyl Urea;

1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-pyridine -3-ylurea;

1-[4-(히드록시메틸)페닐]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;1- [4- (hydroxymethyl) phenyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5- Triazin-2-yl] phenyl} urea;

1-(2-메틸피리딘-4-일)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;1- (2-methylpyridin-4-yl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5- Triazin-2-yl] phenyl} urea;

1-[2-(메틸아미노)에틸]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;1- [2- (methylamino) ethyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-tri Azin-2-yl] phenyl} urea;

1-(3-아세틸페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;1- (3-acetylphenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazine-2 -Yl] phenyl} urea;

1-[4-(디메틸아미노)페닐]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;1- [4- (dimethylamino) phenyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-tri Azin-2-yl] phenyl} urea;

4-[3-{4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐}우레이도]벤조산;4- [3- {4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl} ureido] benzoic acid;

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzamide ;

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드 HCl 염;N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzamide HCl salts;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) Urea;

4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드;4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N-methylbenzamide;

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드;N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N Methylbenzamide;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-모르폴리노피페리딘-1-카르보닐)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-morpholinopiperidine-1-carbonyl) Phenyl) urea;

4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(퀴누클리딘-3-일)벤즈아미드;4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N- (quinuclidin-3-yl) benzamide ;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(피롤리딘-1-일)피페리딘-1-카르보닐)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4- (pyrrolidin-1-yl) piperi Din-1-carbonyl) phenyl) urea;

1-(4-(1,4'-비피페리딘-1'-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (1,4'-bipiperidine-1'-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazine-2- Yl) phenyl) urea;

1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazine-2- Yl) phenyl) urea;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (piperazin-1-carbonyl) phenyl) urea;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(피리딘-2-일)아세틸)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (2- (pyridin-2-yl) acetyl) phenyl) Urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(1-히드록시에틸)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (1-hydroxyethyl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(2-메틸피리딘-4-일)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (2-methylpyridin-4-yl) urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(트리플루오로메틸)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (trifluoromethyl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[2,2,2-트리플루오로-1-히드록시-1-(트리플루오로메틸)에틸]페닐}우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4- [2,2,2-trifluoro- 1-hydroxy-1- (trifluoromethyl) ethyl] phenyl} urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[5-(트리플루오로메틸)피리딘-2-일]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [5- (trifluoromethyl) pyridin-2-yl ] Urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[3-(1-히드록시에틸)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [3- (1-hydroxyethyl) phenyl] urea;

1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -Pyridin-4-ylurea;

1-[4-(2-히드록시에틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;1- [4- (2-hydroxyethyl) phenyl] -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1, 3,5-triazin-2-yl} phenyl) urea;

1-[4-(2-히드록시메틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;1- [4- (2-hydroxymethyl) phenyl] -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1, 3,5-triazin-2-yl} phenyl) urea;

1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(2-메틸피리딘-4-일)우레아;1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -(2-methylpyridin-4-yl) urea;

1-[4-(1-히드록시에틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;1- [4- (1-hydroxyethyl) phenyl] -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1, 3,5-triazin-2-yl} phenyl) urea;

1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

메틸 4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}-아미노)벤조에이트;Methyl 4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} -amino) benzoate;

1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin- 1-yl) carbonyl] phenyl} urea;

4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1- Methylpiperidin-4-yl) benzamide;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(1-메틸피페리딘-4-일)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (1-methylpiperidin-4-yl) urea;

1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(1-메틸피페리딘-4-일)우레아;1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -(1-methylpiperidin-4-yl) urea;

1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아;1- {4- [4- (3,6-Dihydro-2H-pyran-4-yl) -6-morpholin-4-yl- [1,3,5] triazin-2-yl] -phenyl } -3-pyridin-4-yl-urea;

1-{4-[4-모르폴린-4-일-6-(테트라히드로-피란-4-일)-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아;1- {4- [4-morpholin-4-yl-6- (tetrahydro-pyran-4-yl)-[1,3,5] triazin-2-yl] -phenyl} -3-pyridine- 4-yl-urea;

3-({4-모르폴린-4-일-6-[4-(3-피리딘-4-일-우레이도)-페닐]-[1,3,5]트리아진-2-일아미노}-메틸)-아제티딘-1-카르복실산 tert-부틸 에스테르;3-({4-morpholin-4-yl-6- [4- (3-pyridin-4-yl-ureido) -phenyl]-[1,3,5] triazin-2-ylamino}- Methyl) -azetidine-1-carboxylic acid tert-butyl ester;

1-(4-{4-[(아제티딘-3-일메틸)-아미노]-6-모르폴린-4-일-[1,3,5]트리아진-2-일}-페닐)-3-피리딘-4-일-우레아;1- (4- {4-[(azetidin-3-ylmethyl) -amino] -6-morpholin-4-yl- [1,3,5] triazin-2-yl} -phenyl) -3 -Pyridin-4-yl-urea;

1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-pyridin-3-ylurea;

1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-페닐우레아;1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-phenylurea;

1-[4-(디메틸아미노)페닐]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- [4- (dimethylamino) phenyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;

1-(4-시아노페닐)-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- (4-cyanophenyl) -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl-1 , 3,5-triazin-2-yl] phenyl} urea;

1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(2-메틸피리딘-4-일)우레아;1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3- (2-methylpyridin-4-yl) urea;

1-[2-(디메틸아미노)에틸]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- [2- (dimethylamino) ethyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;

1-[4-(4-모르폴린-4-일-6-퀴놀린-3-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-morpholin-4-yl-6-quinolin-3-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

1-[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

메틸 4-({[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;Methyl 4-({[4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate ;

1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin- 1-yl) carbonyl] phenyl} urea;

4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1- Methylpiperidin-4-yl) benzamide;

4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피페리딘-1-일에틸)벤즈아미드;4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (2-piperidine -1-ylethyl) benzamide;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(모르폴린-4-일카르보닐)페닐]우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (morpholin-4-ylcarbonyl) phenyl ] Urea;

1-[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

4-({[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;4-({[4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;

1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl}- 3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;

4-({[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;4-({[4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1-methylpy Ferridin-4-yl) benzamide;

N-[2-(디메틸아미노)에틸]-N-메틸-4-({[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-({[4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) Phenyl] carbamoyl} amino) benzamide;

1-[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;

1-(4-{[3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5 -Triazin-2-yl) phenyl] urea;

1-[4-({4-[2-(디메틸아미노)에틸]피페라진-1-일}카르보닐)페닐]-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- [4-({4- [2- (dimethylamino) ethyl] piperazin-1-yl} carbonyl) phenyl] -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-피롤리딘-1-일피페리딘-1-일)카르보닐]페닐}우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-pyrrolidin-1-ylpy Ferridin-1-yl) carbonyl] phenyl} urea;

4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산; 4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] Carbamoyl} amino) -N-methylbenzamide;

1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] Carbamoyl} amino) benzamide;

4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;

4-({[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산; mp 204℃;4-({[4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid; mp 204 ° C;

1-[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아; mp 170℃;1- [4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methyl Piperazin-1-yl) carbonyl] phenyl} urea; mp 170 ° C .;

4-({[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;4-({[4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [2- (dimethylamino) ethyl] -N-methylbenzamide;

4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [2- (dimethyl Amino) ethyl] -N-methylbenzamide;

1-{4-[4-(1-에톡시비닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (1-ethoxyvinyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea ;

1-[4-(4-아세틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-acetyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

메틸 4-[({4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;Methyl 4-[({4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] Benzoate;

1-{4-[4-(1-히드록시에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (1-hydroxyethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

메틸 4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;Methyl 4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Phenyl} carbamoyl) amino] benzoate;

4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] benzoic acid;

1-(4-{4-모르폴린-4-일-6-[2-(피리딘-4-일아미노)에틸]-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4-morpholin-4-yl-6- [2- (pyridin-4-ylamino) ethyl] -1,3,5-triazin-2-yl} phenyl) -3-pyridine -4-ylurea;

4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[2-(디메틸아미노)에틸]벤즈아미드;4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [2- (dimethyl Amino) ethyl] benzamide;

1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;

1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) benzamide;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4-ethyl-6-morpholin-4-yl-1,3, 5-triazin-2-yl) phenyl] urea;

1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아;1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl] urea;

4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] -N- [2- (dimethylamino) ethyl] -N-methylbenzamide;

1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아;1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-{[4- (dimethylamino) piperi Din-1-yl] carbonyl} phenyl) urea;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) -N-methylbenzamide;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) -N-methylbenzamide;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) benzamide;

4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸-N-[2-(메틸아미노)에틸]벤즈아미드;4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N-methyl-N- [2- (methylamino) ethyl] benzamide;

1-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1 -Yl) carbonyl] phenyl} urea;

1-{4-[(3,3-디메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(3,3-dimethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-methoxy-6-morpholin-4-yl-1,3,5 -Triazin-2-yl) phenyl] urea;

4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피페리딘-1-일에틸)벤즈아미드;4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (2-py Ferridin-1-ylethyl) benzamide;

4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[4-(4-메틸피페라진-1-일)페닐]벤즈아미드;4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [4- (4 -Methylpiperazin-1-yl) phenyl] benzamide;

1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-({[2-(디메틸아미노)에틸]아미노}메틸)페닐]우레아;1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4-({[2- (dimethylamino) ethyl ] Amino} methyl) phenyl] urea;

4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[4-(4-메틸피페라진-1-일)페닐]벤즈아미드;4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [4- (4 -Methylpiperazin-1-yl) phenyl] benzamide;

1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)메틸]페닐}우레아;1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) methyl] phenyl} urea;

1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-포르밀페닐)우레아;1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-formylphenyl) urea;

4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(피리딘-2-일메틸)벤즈아미드;4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (pyridin-2-yl Methyl) benzamide;

1-(4-{4-[2-(1,3-디옥산-2-일)에틸]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4- [2- (1,3-dioxan-2-yl) ethyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea;

1-(4-{4-[2,5-비스(히드록시메틸)피롤리딘-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4- [2,5-bis (hydroxymethyl) pyrrolidin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} Phenyl) -3-pyridin-4-ylurea;

4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-{4-[2-(디메틸아미노)에톡시]페닐}벤즈아미드;4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- {4- [2 -(Dimethylamino) ethoxy] phenyl} benzamide;

1-{4-[(4-벤질피페리딘-1-일)카르보닐]페닐}-3-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(4-benzylpiperidin-1-yl) carbonyl] phenyl} -3- [4- (4-butyl-6-morpholin-4-yl-1,3,5-tri Azin-2-yl) phenyl] urea;

4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1-methylpy Ferridin-4-yl) benzamide;

4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1-methylpy Ferridin-4-yl) benzamide;

1-(4-{4-[3-(디메틸아미노)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4- [3- (dimethylamino) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-yl Urea;

1-[4-(4-{3-[(1-메틸에틸)아미노]프로필}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4- {3-[(1-methylethyl) amino] propyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- Pyridin-4-ylurea;

1-{4-[4-모르폴린-4-일-6-(3-피롤리딘-1-일프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4-morpholin-4-yl-6- (3-pyrrolidin-1-ylpropyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridine- 4-ylurea;

1-(4-{4-[3-(4-메틸피페라진-1-일)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4- [3- (4-methylpiperazin-1-yl) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl)- 3-pyridin-4-ylurea;

1-{4-[4-(3-{[2-(디메틸아미노)에틸]아미노}프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (3-{[2- (dimethylamino) ethyl] amino} propyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-(3-히드록시프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (3-hydroxypropyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-모르폴린-4-일-6-(3-옥소프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4-morpholin-4-yl-6- (3-oxopropyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아;1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl}- 3- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) urea;

4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]벤즈아미드;4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] -N- [2- (dimethylamino) ethyl] benzamide;

1-[4-(4-메틸피페라진-1-일)페닐]-3-[4-(4-모르폴린-4-일-6-프로필-1,3,5-트리아진-2-일)페닐]우레아;1- [4- (4-methylpiperazin-1-yl) phenyl] -3- [4- (4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-yl ) Phenyl] urea;

1-{4-[2-(디메틸아미노)에톡시]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4- [2- (dimethylamino) ethoxy] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) Phenyl] urea;

1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(4-메틸피페라진-1-일)페닐]우레아;1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (4-methylpiperazin-1-yl ) Phenyl] urea;

1-[4-(4-메틸피페라진-1-일)페닐]-3-{4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- [4- (4-methylpiperazin-1-yl) phenyl] -3- {4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3,5-tri Azin-2-yl] phenyl} urea;

1-{4-[(3,3-디메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(3,3-dimethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3,5- Triazin-2-yl) phenyl] urea;

4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸아제티딘-3-일)벤즈아미드;4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1-methylase Thidin-3-yl) benzamide;

메틸 4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;Methyl 4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate ;

N-[2-(디메틸아미노)에틸]-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl ] Phenyl} carbamoyl) amino] benzamide;

N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazine -2-yl] phenyl} carbamoyl) amino] benzamide;

N-(1-메틸아제티딘-3-일)-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- (1-methylazetidin-3-yl) -4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazine-2 -Yl] phenyl} carbamoyl) amino] benzamide;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4- (1-methylethyl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;

4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-피리딘-4-일벤즈아미드;4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] -N- Pyridin-4-ylbenzamide;

4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-피리딘-3-일벤즈아미드;4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] -N- Pyridin-3-ylbenzamide;

N-시클로부틸-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N-cyclobutyl-4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) Amino] benzamide;

1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-페닐피페리딘-1-일)카르보닐]페닐}우레아;1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-phenylpiperidine-1 -Yl) carbonyl] phenyl} urea;

4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(피리딘-4-일메틸)벤즈아미드;4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (pyridine-4- Monomethyl) benzamide;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3 , 5-triazin-2-yl] phenyl} urea;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4- (2-methylpropyl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;

N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3,5-triazine -2-yl] phenyl} carbamoyl) amino] benzamide;

1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- {4-[(4-methylpipepe Razin-1-yl) carbonyl] phenyl} urea;

N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;

1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3, 5-triazin-2-yl] phenyl} urea;

1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazine -2-yl) phenyl] urea;

4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;

1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-[4-(4-메틸피페라진-1-일)페닐]우레아;1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- [4- (4-methylpiperazin -1-yl) phenyl] urea;

메틸 4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;Methyl 4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate;

1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]우레아;1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazine -2-yl) phenyl] urea;

1-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea ;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-3-yl) urea ;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpipepe Razin-1-yl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-일)피리딘-3-일)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (6- (4-methylpipepe Razin-1-yl) pyridin-3-yl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-((디메틸아미노)메틸)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4-((dimethylamino) Methyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)에톡시)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2- (dimethyl Amino) ethoxy) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(피롤리딘-1-일)에톡시)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2- (pi Ralidin-1-yl) ethoxy) phenyl) urea;

(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (pyridin-3-yl) urea;

(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아;(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea;

(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-일)페닐)우레아;(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4- (piperazin-1-yl) phenyl) urea;

1-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-((S)-3-메틸피페라진-1-일)페닐)우레아;1- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4-((S) -3-methylpiperazin-1-yl) phenyl) urea;

1-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-((R)-3-메틸피페라진-1-일)페닐)우레아;1- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4-((R) -3-methylpiperazin-1-yl) phenyl) urea;

1-(4-((3R,5S)-3,5-디메틸피페라진-1-일)페닐)-3-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4-((3R, 5S) -3,5-dimethylpiperazin-1-yl) phenyl) -3- (4- (4-((R) -3-methylmorpholino) -6- (Tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(2-(디메틸아미노)에톡시)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (2- (dimethylamino) ethoxy) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4 -Yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(4-에틸피페라진-1-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (4-ethylpiperazin-1-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran- 4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(4-이소프로필피페라진-1-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (4-isopropylpiperazin-1-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran -4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro- 2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

(R)-1-(4-(4-이소프로필피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-일)피리딘-3-일)우레아;(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (6- (4-methylpiperazin-1-yl) pyridin-3-yl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-ethylpipepe Razin-1-yl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-일)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropyl Piperazin-1-yl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethyl Amino) piperidin-1-yl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpipepe Razin-1-carbonyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropyl Piperazine-1-carbonyl) phenyl) urea;

4-(3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레이도)-N,N-디메틸벤즈아미드;4- (3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) ureido) -N, N- Dimethylbenzamide;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피롤리딘-1-일메틸)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (pyrrolidine- 1-ylmethyl) phenyl) urea;

4-({[4-(4-{4-[(메틸카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;4-({[4- (4- {4-[(methylcarbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) benzamide;

1-{4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;1- {4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-triazine-2- Il] phenyl} -3-pyridin-3-ylurea;

3-({[4-(4-{4-[(메틸카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;3-({[4- (4- {4-[(methylcarbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) benzamide;

1-메틸-3-[4-(4-모르폴린-4-일-6-{4-[(피리딘-3-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)페닐]우레아;1-methyl-3- [4- (4-morpholin-4-yl-6- {4-[(pyridin-3-ylcarbamoyl) amino] phenyl} -1,3,5-triazine-2 -Yl) phenyl] urea;

1-메틸-3-[4-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)페닐]우레아;1-methyl-3- [4- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazine-2 -Yl) phenyl] urea;

3-[({4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;3-[({4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;

4-[({4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;4-[({4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;

1-{4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-triazine-2- Il] phenyl} -3-pyridin-4-ylurea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-메틸우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-methylurea;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4-morpholin-4-yl-6-[(3S) -tetrahydrofuran-3 -Yloxy] -1,3,5-triazin-2-yl} phenyl) urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리다진-4-일우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridazin-4-ylurea;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(옥세탄-3-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (oxetan-3-yloxy)- 1,3,5-triazin-2-yl] phenyl} urea;

1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;

1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;

1-[4-(4-이소프로필-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-isopropyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1 -Yl) carbonyl] phenyl} urea;

1-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-피리미딘-5-일페닐)우레아;1- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-pyrimidine-5- Phenyl) urea;

1-(4-{4-[(2,2-디메톡시에틸)아미노]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아;1- (4- {4-[(2,2-dimethoxyethyl) amino] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridine- 3-ylurea;

1-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-피리딘-4-일페닐)우레아;1- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-pyridin-4-yl Phenyl) urea;

1-(4-요오도페닐)-3-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- (4-iodophenyl) -3- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} urea ;

1-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;1- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-{[4- ( 1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;

1-[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;1- [4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-{[4- ( 1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;

1-{4-[2-(디메틸아미노)피리미딘-5-일]페닐}-3-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- {4- [2- (dimethylamino) pyrimidin-5-yl] phenyl} -3- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3, 5-triazin-2-yl] phenyl} urea;

tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]아제티딘-1-카르복실레이트;tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) Oxy] azetidine-1-carboxylate;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5 -Triazin-2-yl) phenyl] urea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-니트로페닐)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-nitrophenyl) urea;

1-(4-아미노페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-aminophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea;

N-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-4-메틸피페라진-1-카르복스아미드;N- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) phenyl] -4-methyl Piperazine-1-carboxamide;

4-(디메틸아미노)-N-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]피페리딘-1-카르복스아미드;4- (dimethylamino) -N- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino ) Phenyl] piperidine-1-carboxamide;

1-[2-(디메틸아미노)에틸]-3-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-1-메틸우레아;1- [2- (dimethylamino) ethyl] -3- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] Carbamoyl} amino) phenyl] -1-methylurea;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-{[(2-피페리딘-1-일에틸)카르바모일]아미노}페닐)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-{[(2-piperidin-1- One ethyl) carbamoyl] amino} phenyl) urea;

N-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-4-메틸-1,4-디아제판-1-카르복스아미드;N- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) phenyl] -4-methyl -1,4-diazepane-1-carboxamide;

N-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-4-에틸피페라진-1-카르복스아미드;N- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) phenyl] -4-ethyl Piperazine-1-carboxamide;

1-{4-[(디메틸카르바모일)아미노]페닐}-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(dimethylcarbamoyl) amino] phenyl} -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] Urea;

1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아;1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl}- 3- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) urea;

4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] -N- [2- (dimethylamino) ethyl] -N-methylbenzamide;

1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl}- 3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;

4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]벤즈아미드;4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] -N- [2- (dimethylamino) ethyl] benzamide;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;

N-[2-(디메틸아미노)에틸]-4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1,3,5- Triazin-2-yl] phenyl} carbamoyl) amino] benzamide;

4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-(2-피롤리딘-1-일에틸)벤즈아미드;4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} carbamoyl ) Amino] -N- (2-pyrrolidin-1-ylethyl) benzamide;

4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-(2-피페리딘-1-일에틸)벤즈아미드;4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} carbamoyl ) Amino] -N- (2-piperidin-1-ylethyl) benzamide;

1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-{[4- (1-methylethyl) pipe Razin-1-yl] carbonyl} phenyl) urea;

N-[2-(디메틸아미노)에틸]-N-메틸-4-{[(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-{[(4- {4-morpholin-4-yl-6-[(3S) -tetrahydrofuran-3-yloxy]- 1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

4-{[(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-피페리딘-1-일에틸)벤즈아미드;4-{[(4- {4-morpholin-4-yl-6-[(3S) -tetrahydrofuran-3-yloxy] -1,3,5-triazin-2-yl} phenyl) carr Barmoyl] amino} -N- (2-piperidin-1-ylethyl) benzamide;

4-{[(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-피롤리딘-1-일에틸)벤즈아미드;4-{[(4- {4-morpholin-4-yl-6-[(3S) -tetrahydrofuran-3-yloxy] -1,3,5-triazin-2-yl} phenyl) carr Barmoyl] amino} -N- (2-pyrrolidin-1-ylethyl) benzamide;

1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)우레아;1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- (4- {4-morpholin-4-yl-6-[(3S)- Tetrahydrofuran-3-yloxy] -1,3,5-triazin-2-yl} phenyl) urea;

1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H -Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;

N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1, 3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide;

4-[({4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;4-[({4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;

1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-[4-(4-메틸피페라진-1-일)페닐]우레아;1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- [4- (4-methylpiperazin -1-yl) phenyl] urea;

4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;

메틸 4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;Methyl 4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate;

1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazine -2-yl) phenyl] urea;

1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3, 5-triazin-2-yl] phenyl} urea;

N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;

1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- {4-[(4-methylpipepe Razin-1-yl) carbonyl] phenyl} urea;

1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-피리딘-2-일피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-pyridin-2-ylpipepe Razin-1-yl) carbonyl] phenyl} urea;

1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]우레아;1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazine -2-yl) phenyl] urea;

1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;

1-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

메틸 4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;Methyl 4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;

N-[2-(디메틸아미노)에틸]-N-메틸-4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) Phenyl] carbamoyl} amino) benzamide;

메틸 4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;Methyl 4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino } Benzoate;

4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;

N-[2-(디메틸아미노)에틸]-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Phenyl} carbamoyl) amino] benzamide;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazine -2-yl) phenyl] urea;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-phenyl-1,3, 5-triazin-2-yl) phenyl] urea;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) benzamide;

4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-[2-(디메틸아미노)에틸]벤즈아미드;4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- [2- (dimethylamino) ethyl] benzamide;

1-{4-[(4-이소프로필피페라진-1-일)카르보닐]페닐}-3-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- {4-[(4-isopropylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3 , 5-triazin-2-yl] phenyl} urea;

4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-(2-피롤리딘-1-일에틸)벤즈아미드;4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] -N- ( 2-pyrrolidin-1-ylethyl) benzamide;

4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} Benzoic acid;

N-(2-메톡시에틸)-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- (2-methoxyethyl) -4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} Carbamoyl) amino] benzamide;

N-(2-메톡시에틸)-4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- (2-methoxyethyl) -4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} Amino) benzamide;

4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피롤리딘-1-일에틸)벤즈아미드;4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (2-pyrroli Din-1-ylethyl) benzamide;

1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-[4-(피롤리딘-1-일카르보닐)페닐]우레아;1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- [4- (pyrrolidine-1 -Ylcarbonyl) phenyl] urea;

N-[3-(디메틸아미노)프로필]-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [3- (dimethylamino) propyl] -4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Phenyl} carbamoyl) amino] benzamide;

1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-[4-(피페리딘-1-일카르보닐)페닐]우레아;1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- [4- (piperidine-1 -Ylcarbonyl) phenyl] urea;

N-[3-(디메틸아미노)프로필]-4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [3- (dimethylamino) propyl] -4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) benzamide;

1-{4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (2-thienyl) -1,3 , 5-triazin-2-yl] phenyl} urea;

메틸 4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;Methyl 4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate ;

N-(2-메톡시에틸)-4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- (2-methoxyethyl) -4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] benzamide;

N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazine -2-yl] phenyl} carbamoyl) amino] benzamide;

N-[2-(디메틸아미노)에틸]-4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl ] Phenyl} carbamoyl) amino] benzamide;

4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- [2- (dimethylamino) ethyl] -N-methylbenzamide;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-methylpiperazin-1-yl) carbonyl] phenyl} urea;

1-{4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1,3,5-triazin-2-yl] phenyl} -3-pyridine- 4-ylurea;

메틸 4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;Methyl 4-[({4- [4-morpholin-4-yl-6- (1,4-oxazapan-4-yl) -1,3,5-triazin-2-yl] phenyl} carba Moyl) amino] benzoate;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl} urea;

4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;4-[({4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1,3,5-triazin-2-yl] phenyl} carbamoyl ) Amino] benzoic acid;

N-[3-(디메틸아미노)프로필]-4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [3- (dimethylamino) propyl] -4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl ] Phenyl} carbamoyl) amino] benzamide;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-[4-(피롤리딘-1-일카르보닐)페닐]우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- [4- (pi Rollidin-1-ylcarbonyl) phenyl] urea;

N-[2-(디메틸아미노)에틸]-4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -4-[({4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1,3,5- Triazin-2-yl] phenyl} carbamoyl) amino] benzamide;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (1,4-oxazapan-4- Yl) -1,3,5-triazin-2-yl] phenyl} urea;

N-(2-메톡시에틸)-4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- (2-methoxyethyl) -4-[({4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1,3,5-triazine -2-yl] phenyl} carbamoyl) amino] benzamide;

1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}우레아;1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (2-thienyl) -1,3 , 5-triazin-2-yl] phenyl} urea;

1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{3-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- {3-[(4-methylpipepe Razin-1-yl) carbonyl] phenyl} urea;

3-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;3-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;

메틸 3-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;Methyl 3-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate;

1-(3-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- (3-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4- (4-methylphenyl) -6-morpholin-4-yl- 1,3,5-triazin-2-yl] phenyl} urea;

N-[2-(디메틸아미노)에틸]-N-메틸-3-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-3-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;

메틸 3-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;Methyl 3-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;

메틸 3-({[4-(4-모르폴린-4-일-6-티오펜-2-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;Methyl 3-({[4- (4-morpholin-4-yl-6-thiophen-2-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate ;

N-[2-(디메틸아미노)에틸]-3-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -3-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Phenyl} carbamoyl) amino] benzamide;

N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1, 3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide;

3-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;3-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;

메틸 3-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;Methyl 3-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;

1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{3-[(4-피리딘-2-일피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {3-[(4-pyridin-2-ylpipepe Razin-1-yl) carbonyl] phenyl} urea;

N-[2-(디메틸아미노)에틸]-3-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;N- [2- (dimethylamino) ethyl] -3-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) -N-methylbenzamide;

1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{3-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {3-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;

3-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;3-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;

메틸 4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;Methyl 4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzo Eight;

1-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;

메틸 4-({[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;Methyl 4-({[4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzo Eight;

1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-piperidine-1 -Yl-1,3,5-triazin-2-yl) phenyl] urea;

1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-piperidin-1-yl-1, 3,5-triazin-2-yl) phenyl] urea;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-piperidin-1-yl-1, 3,5-triazin-2-yl) phenyl] urea;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-piperidine-1- Yl-1,3,5-triazin-2-yl) phenyl] urea;

4-({[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;4-({[4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;

1-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazine-2- Yl) phenyl] carbamoyl} amino) benzamide;

1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-pyrrolidine-1- Yl-1,3,5-triazin-2-yl) phenyl] urea;

1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-pyrrolidine-1 -Yl-1,3,5-triazin-2-yl) phenyl] urea;

N-[2-(디메틸아미노)에틸]-N-메틸-4-({[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-({[4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-tri Azin-2-yl) phenyl] carbamoyl} amino) benzamide;

N-[2-(디메틸아미노)에틸]-N-메틸-4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-tri Azin-2-yl) phenyl] carbamoyl} amino) benzamide;

1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1, 3,5-triazin-2-yl) phenyl] urea;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1, 3,5-triazin-2-yl) phenyl] urea;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazine-2- Yl) phenyl] carbamoyl} amino) benzamide;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-yl Urea;

N-[3-(디메틸아미노)프로필]-4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [3- (dimethylamino) propyl] -4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazine-2- Yl) phenyl] carbamoyl} amino) benzamide;

N-(2-메톡시에틸)-4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- (2-methoxyethyl) -4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazin-2-yl) Phenyl] carbamoyl} amino) benzamide;

1-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]-3-[4-(피롤리딘-1-일카르보닐)페닐]우레아;1- [4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (pyrrolidine -1-ylcarbonyl) phenyl] urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-ethylpiperazin-1-yl) carbonyl] phenyl} urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;

메틸 4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;Methyl 4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} benzoate;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) urea;

1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -{4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;

1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- (4- {4-[(3S) -3-methylmorpholin-4-yl ] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;

4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) Carbamoyl] amino} benzoic acid;

1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-mor Folin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;

N-[3-(디메틸아미노)프로필]-4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [3- (dimethylamino) propyl] -4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3 , 5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-피롤리딘-1-일에틸)벤즈아미드;4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) Carbamoyl] amino} -N- (2-pyrrolidin-1-ylethyl) benzamide;

1-(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- (4- {4-[(3R) -3-methylmorpholin-4-yl] -6-[(3S) -3-methylmorpholin-4-yl] -1,3,5-triazine -2-yl} phenyl) -3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(디프로필아미노)피페리딘-1-일]카르보닐}페닐)우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (dipropylamino) piperidin-1-yl] carbonyl} phenyl) urea;

1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)우레아;1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4-[(3R) -3-methylmorpholin-4-yl] -6- [ (3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) urea;

4-{[(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;4-{[(4- {4-[(3R) -3-methylmorpholin-4-yl] -6-[(3S) -3-methylmorpholin-4-yl] -1,3,5- Triazin-2-yl} phenyl) carbamoyl] amino} benzoic acid;

1-{4-[(4-부틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)우레아;1- {4-[(4-butylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4-[(3R) -3-methylmorpholin-4-yl] -6- [ (3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) urea;

메틸 4-{[(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;Methyl 4-{[(4- {4-[(3R) -3-methylmorpholin-4-yl] -6-[(3S) -3-methylmorpholin-4-yl] -1,3,5 -Triazin-2-yl} phenyl) carbamoyl] amino} benzoate;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-부틸피페라진-1-일)카르보닐]페닐}우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-butylpiperazin-1-yl) carbonyl] phenyl} urea;

1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)우레아;1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- (4- {4-[(3R) -3-methylmorpholin-4-yl ] -6-[(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(2-메틸프로필)피페라진-1-일]카르보닐}페닐)우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (2-methylpropyl) piperazin-1-yl] carbonyl} phenyl) urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸프로필)피페라진-1-일]카르보닐}페닐)우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (1-methylpropyl) piperazin-1-yl] carbonyl} phenyl) urea;

4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-[2-(4-메틸피페라진-1-일)에틸]벤즈아미드;4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- [2- (4-methylpiperazin-1-yl) ethyl] benzamide;

N-[2-(디메틸아미노)에틸]-4-{[(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [2- (dimethylamino) ethyl] -4-{[(4- {4-[(3R) -3-methylmorpholin-4-yl] -6-[(3S) -3-methylmorpholine -4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-피롤리딘-1-일에틸)벤즈아미드;4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- (2-pyrrolidin-1-ylethyl) benzamide;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-프로필피페리딘-1-일)카르보닐]페닐}우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-propylpiperidin-1-yl) carbonyl] phenyl} urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-[4-(피페리딘-1-일카르보닐)페닐]우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- [4- (pi Ferridin-1-ylcarbonyl) phenyl] urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-프로필피페라진-1-일)카르보닐]페닐}우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-propylpiperazin-1-yl) carbonyl] phenyl} urea;

4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-메톡시에틸)벤즈아미드;4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- (2-methoxyethyl) benzamide;

1-{4-[4-모르폴린-4-일-6-(4-트리시클로[3.3.1.13,7]데크-1-일피페라진-1-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4-morpholin-4-yl-6- (4-tricyclo [3.3.1.13,7] dec-1-ylpiperazin-1-yl) -1,3,5-triazine -2-yl] phenyl} -3-pyridin-4-ylurea;

메틸 4-{[(4-{4-[4-(디메틸카르바모일)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;Methyl 4-{[(4- {4- [4- (dimethylcarbamoyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} Phenyl) carbamoyl] amino} benzoate;

N,N-디메틸-4-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)피페라진-1-카르복스아미드;N, N-dimethyl-4- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazine-2- (1) piperazine-1-carboxamide;

N,N-디메틸-4-(4-{4-[({4-[(4-메틸피페라진-1-일)카르보닐]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)피페라진-1-카르복스아미드;N, N-dimethyl-4- (4- {4-[({4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} carbamoyl) amino] phenyl} -6-morpholine- 4-yl-1,3,5-triazin-2-yl) piperazin-1-carboxamide;

N,N-디메틸-4-{4-모르폴린-4-일-6-[4-({[4-(피리다진-4-일카르바모일)페닐]카르바모일}아미노)페닐]-1,3,5-트리아진-2-일}피페라진-1-카르복스아미드;N, N-dimethyl-4- {4-morpholin-4-yl-6- [4-({[4- (pyridazin-4-ylcarbamoyl) phenyl] carbamoyl} amino) phenyl]- 1,3,5-triazin-2-yl} piperazine-1-carboxamide;

N,N-디메틸-4-(4-모르폴린-4-일-6-{4-[({4-[(4-프로필피페리딘-1-일)카르보닐]페닐}카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)피페라진-1-카르복스아미드;N, N-dimethyl-4- (4-morpholin-4-yl-6- {4-[({4-[(4-propylpiperidin-1-yl) carbonyl] phenyl} carbamoyl) Amino] phenyl} -1,3,5-triazin-2-yl) piperazine-1-carboxamide;

4-{[(4-{4-[4-(디메틸카르바모일)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;4-{[(4- {4- [4- (dimethylcarbamoyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} benzoic acid;

4-(4-{4-[({4-[(2-메톡시에틸)카르바모일]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)-N,N-디메틸피페라진-1-카르복스아미드;4- (4- {4-[({4-[(2-methoxyethyl) carbamoyl] phenyl} carbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5 -Triazin-2-yl) -N, N-dimethylpiperazin-1-carboxamide;

4-[4-(4-{[(4-{[2-(디메틸아미노)에틸](메틸)카르바모일}페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]-N,N-디메틸피페라진-1-카르복스아미드;4- [4- (4-{[(4-{[2- (dimethylamino) ethyl] (methyl) carbamoyl} phenyl) carbamoyl] amino} phenyl) -6-morpholin-4-yl- 1,3,5-triazin-2-yl] -N, N-dimethylpiperazin-1-carboxamide;

4-(4-{4-[({4-[(4-에틸피페라진-1-일)카르보닐]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)-N,N-디메틸피페라진-1-카르복스아미드;4- (4- {4-[({4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} carbamoyl) amino] phenyl} -6-morpholin-4-yl-1, 3,5-triazin-2-yl) -N, N-dimethylpiperazin-1-carboxamide;

1-(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -Pyridin-4-ylurea;

메틸 4-{[(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;Methyl 4-{[(4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} benzoate;

4-{[(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;4-{[(4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) Carbamoyl] amino} benzoic acid;

N-[3-(디메틸아미노)프로필]-4-{[(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [3- (dimethylamino) propyl] -4-{[(4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3 , 5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

N-[2-(디메틸아미노)에틸]-4-{[(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [2- (dimethylamino) ethyl] -4-{[(4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3 , 5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

4-{[(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;4-{[(4- {4- [4- (1-methylethyl) -1,4-diazepane-1-yl] -6-morpholin-4-yl-1,3,5-triazine- 2-yl} phenyl) carbamoyl] amino} benzoic acid;

메틸 4-{[(4-{4-[4-(아세틸아미노)피페리딘-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;Methyl 4-{[(4- {4- [4- (acetylamino) piperidin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} benzoate;

1-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- (4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholin-4-yl-1,3,5-triazine-2- Il} phenyl) -3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;

N-[1-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)피페리딘-4-일]아세트아미드;N- [1- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) pi Ferridin-4-yl] acetamide;

4-{[(4-{4-[4-(아세틸아미노)피페리딘-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;4-{[(4- {4- [4- (acetylamino) piperidin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) Carbamoyl] amino} benzoic acid;

N-[2-(디메틸아미노)에틸]-4-{[(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [2- (dimethylamino) ethyl] -4-{[(4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholine-4 -Yl-1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

N-{1-[(4-{[(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}페닐)카르보닐]피페리딘-4-일}아세트아미드;N- {1-[(4-{[(4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholin-4-yl-1, 3,5-triazin-2-yl} phenyl) carbamoyl] amino} phenyl) carbonyl] piperidin-4-yl} acetamide;

1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4- [4- (1-methylethyl) -1,4-diazepane-1- Il] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;

1-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;1- (4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholin-4-yl-1,3,5-triazine-2- Il} phenyl) -3- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[(3S)-3-메틸모르폴린-4-일]카르보닐}페닐)우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ (3S) -3-methylmorpholin-4-yl] carbonyl} phenyl) urea;

1-{4-[(4-부틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;1- {4-[(4-butylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4- [4- (1-methylethyl) -1,4-diazepane-1- Il] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;

1-(4-{4-[(4-메틸피페라진-1-일)아미노]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-페닐우레아;1- (4- {4-[(4-methylpiperazin-1-yl) amino] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3- Phenylurea;

1-(4-{4-[(1-메틸피페리딘-4-일)옥시]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4-[(1-methylpiperidin-4-yl) oxy] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -Pyridin-4-ylurea;

1-{4-[4-모르폴린-4-일-6-(피페리딘-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4-morpholin-4-yl-6- (piperidin-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-pyridine-4- Ilurea;

에틸 4-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]피페리딘-1-카르복실레이트;Ethyl 4-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) oxy] Piperidine-1-carboxylate;

N-에틸-4-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]피페리딘-1-카르복스아미드;N-ethyl-4-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl ) Oxy] piperidine-1-carboxamide;

tert-부틸 4-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]피페리딘-1-카르복실레이트;tert-butyl 4-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) Oxy] piperidine-1-carboxylate;

4-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]피페리딘-1-술폰아미드;4-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) oxy] py Ferridine-1-sulfonamide;

1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-pyridin-3-ylurea;

1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-페닐우레아;1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-phenylurea;

1-[4-(디메틸아미노)페닐]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- [4- (dimethylamino) phenyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;

1-(4-시아노페닐)-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- (4-cyanophenyl) -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl-1 , 3,5-triazin-2-yl] phenyl} urea;

1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(2-메틸피리딘-4-일)우레아;1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3- (2-methylpyridin-4-yl) urea;

1-[2-(디메틸아미노)에틸]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;1- [2- (dimethylamino) ethyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;

1-[4-(4-모르폴린-4-일-6-퀴놀린-3-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4-morpholin-4-yl-6-quinolin-3-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;

1-{4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea ;

메틸 4-[({4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;Methyl 4-[({4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] Benzoate;

1-(4-{4-모르폴린-4-일-6-[2-(피리딘-4-일아미노)에틸]-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4-morpholin-4-yl-6- [2- (pyridin-4-ylamino) ethyl] -1,3,5-triazin-2-yl} phenyl) -3-pyridine -4-ylurea;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) -N-methylbenzamide;

N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) benzamide;

4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸-N-[2-(메틸아미노)에틸]벤즈아미드;4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N-methyl-N- [2- (methylamino) ethyl] benzamide;

1-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- [4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1 -Yl) carbonyl] phenyl} urea;

1-{4-[(3,3-디메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(3,3-dimethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-methoxy-6-morpholin-4-yl-1,3,5 -Triazin-2-yl) phenyl] urea;

4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피페리딘-1-일에틸)벤즈아미드;4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (2-py Ferridin-1-ylethyl) benzamide;

1-(4-{4-[2,5-비스(히드록시메틸)피롤리딘-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4- [2,5-bis (hydroxymethyl) pyrrolidin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} Phenyl) -3-pyridin-4-ylurea;

1-(4-{4-[2-(1,3-디옥산-2-일)에틸]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4- [2- (1,3-dioxan-2-yl) ethyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea;

1-(4-{4-[3-(디메틸아미노)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4- [3- (dimethylamino) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-yl Urea;

1-[4-(4-{3-[(1-메틸에틸)아미노]프로필}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;1- [4- (4- {3-[(1-methylethyl) amino] propyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- Pyridin-4-ylurea;

1-{4-[4-모르폴린-4-일-6-(3-피롤리딘-1-일프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4-morpholin-4-yl-6- (3-pyrrolidin-1-ylpropyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridine- 4-ylurea;

1-(4-{4-[3-(4-메틸피페라진-1-일)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;1- (4- {4- [3- (4-methylpiperazin-1-yl) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl)- 3-pyridin-4-ylurea;

1-{4-[4-(3-{[2-(디메틸아미노)에틸]아미노}프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (3-{[2- (dimethylamino) ethyl] amino} propyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-(3-히드록시프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (3-hydroxypropyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

1-{4-[4-모르폴린-4-일-6-(3-옥소프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4-morpholin-4-yl-6- (3-oxopropyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;

N-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)벤젠술폰아미드;N- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) benzenesulfonamide;

N-{4-[4-({[4-(4-메틸피페라진-1-일)페닐]카르바모일}아미노)페닐]-6-모르폴린-4-일-1,3,5-트리아진-2-일}벤젠술폰아미드;N- {4- [4-({[4- (4-methylpiperazin-1-yl) phenyl] carbamoyl} amino) phenyl] -6-morpholin-4-yl-1,3,5- Triazin-2-yl} benzenesulfonamide;

N-(4-{4-[({4-[2-(디메틸아미노)에톡시]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)벤젠술폰아미드;N- (4- {4-[({4- [2- (dimethylamino) ethoxy] phenyl} carbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-tri Azin-2-yl) benzenesulfonamide;

N-(4-{4-[({4-[(4-메틸피페라진-1-일)카르보닐]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)벤젠술폰아미드;N- (4- {4-[({4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} carbamoyl) amino] phenyl} -6-morpholin-4-yl-1, 3,5-triazin-2-yl) benzenesulfonamide;

N-{4-모르폴린-4-일-6-[4-({[4-(피페라진-1-일카르보닐)페닐]카르바모일}아미노)페닐]-1,3,5-트리아진-2-일}벤젠술폰아미드;N- {4-morpholin-4-yl-6- [4-({[4- (piperazin-1-ylcarbonyl) phenyl] carbamoyl} amino) phenyl] -1,3,5-tri Azin-2-yl} benzenesulfonamide;

N-[4-(4-{[(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]벤젠술폰아미드;N- [4- (4-{[(4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) carbamoyl] amino} phenyl) -6-morpholine-4- Yl-1,3,5-triazin-2-yl] benzenesulfonamide;

N-[2-(디메틸아미노)에틸]-N-메틸-4-{[(4-{4-모르폴린-4-일-6-[(페닐술포닐)아미노]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-{[(4- {4-morpholin-4-yl-6-[(phenylsulfonyl) amino] -1,3,5- Triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

N-[2-(디메틸아미노)에틸]-4-{[(4-{4-모르폴린-4-일-6-[(페닐술포닐)아미노]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [2- (dimethylamino) ethyl] -4-{[(4- {4-morpholin-4-yl-6-[(phenylsulfonyl) amino] -1,3,5-triazine-2 -Yl} phenyl) carbamoyl] amino} benzamide;

메틸 4-{[(4-{4-모르폴린-4-일-6-[(페닐술포닐)아미노]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;Methyl 4-{[(4- {4-morpholin-4-yl-6-[(phenylsulfonyl) amino] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} Benzoate;

4-{[(4-{4-모르폴린-4-일-6-[(페닐술포닐)아미노]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;4-{[(4- {4-morpholin-4-yl-6-[(phenylsulfonyl) amino] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzoic acid ;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-[4-(6-모르폴린-4-일-4-옥소-4,5-디히드로-1,3,5-트리아진-2-일)페닐]우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (6-morpholin-4-yl-4-oxo-4,5-dihydro-1 , 3,5-triazin-2-yl) phenyl] urea;

1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) Phenyl) urea;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필-2-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropyl-2-methylpiperazin-1- Carbonyl) phenyl) urea;

1-(4-(4-시클로부틸-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazine-2 -Yl) phenyl) urea;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필-3-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropyl-3-methylpiperazin-1- Carbonyl) phenyl) urea;

1-(4-(3,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) Phenyl) urea;

1-(4-(4-시클로부틸-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazine-2 -Yl) phenyl) urea;

1-(4-(4-시클로부틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl Urea;

1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-이소프로필-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-isopropyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl ) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-시클로부틸-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl ) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-이소프로필-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-isopropyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl ) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(3,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-시클로부틸-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl ) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-시클로부틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1, 3,5-triazin-2-yl) phenyl) urea;

1-(4-(2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1,3 , 5-triazin-2-yl) phenyl) urea;

1-(4-(3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1,3 , 5-triazin-2-yl) phenyl) urea;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3-methylpiperazin-1-carbonyl) phenyl) Urea;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(2-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (2-methylpiperazin-1-carbonyl) phenyl) Urea;

1-(4-(3,3-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3,3-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) Phenyl) urea;

1-(4-(3,3-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3,3-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(3,3,4-트리메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) -3- (4- (3 , 3,4-trimethylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3,3,4-트리메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3,3,4-trimethylpiperazin-1-car Carbonyl) phenyl) urea;

1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-이소프로필-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-isopropyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-시클로부틸-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-이소프로필-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-isopropyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(3,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4 -Yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-시클로부틸-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-시클로부틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutylpiperazine-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4- Yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(3,3,4-트리메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) -3- (4- (3,3,4-trimethylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(3,3-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3,3-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4 -Yl) -1,3,5-triazin-2-yl) phenyl) urea;

N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) ureido) benzamide;

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3 , 5-triazin-2-yl) phenyl) ureido) benzamide;

1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran -4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5 -Triazin-2-yl) phenyl) urea;

1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5 -Triazin-2-yl) phenyl) urea;

1-(4-(4-이소프로필-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-isopropyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1, 3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-시클로부틸-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1, 3,5-triazin-2-yl) phenyl) urea;

N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5-triazine -2-yl) phenyl) ureido) benzamide;

1-(4-(4-이소프로필-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-isopropyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1, 3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3-methylpiperazin -1-carbonyl) phenyl) urea;

1-(4-(3,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5 -Triazin-2-yl) phenyl) urea;

1-(4-(4-시클로부틸-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1, 3,5-triazin-2-yl) phenyl) urea;

1-(4-(3,3-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3,3-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5 -Triazin-2-yl) phenyl) urea;

1-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3,3,4-트리메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3,3,4 -Trimethylpiperazine-1-carbonyl) phenyl) urea;

1-(4-(4-시클로부틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclobutylpiperazine-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5- Triazin-2-yl) phenyl) urea;

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5-triazin-2-yl ) Phenyl) ureido) benzamide;

1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3 , 5-triazin-2-yl) phenyl) urea;

1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3 , 5-triazin-2-yl) phenyl) urea;

1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran -4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아;1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea;

1-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl ) -6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(퀴누클리딘-4-일)페닐)우레아;1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (quinucridin-4-yl) phenyl) urea;

1-(4-(4-시클로프로필피페라진-1-일)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclopropylpiperazin-1-yl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6 -((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(시클로프로필메틸)피페라진-1-일)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (cyclopropylmethyl) piperazin-1-yl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl ) -6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아;1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-yl) phenyl) urea;

1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-일)페닐)우레아;1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-yl) phenyl) urea;

1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazine-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidine-1- Yl) -6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-시클로프로필피페라진-1-카르보닐)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-cyclopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl)- 6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(시클로프로필메틸)피페라진-1-카르보닐)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (cyclopropylmethyl) piperazin-1-carbonyl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidine-1- Yl) -6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(퀴누클리딘-4-일)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (quinucridin-4-yl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-시클로프로필피페라진-1-일)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-cyclopropylpiperazin-1-yl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(시클로프로필메틸)피페라진-1-일)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4- (cyclopropylmethyl) piperazin-1-yl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-yl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-일)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-yl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-시클로프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-cyclopropylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(시클로프로필메틸)피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4- (cyclopropylmethyl) piperazin-1-carbonyl) phenyl) urea;

1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) Urea;

1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-3-yl) Urea;

1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (pyridazin-4-yl Urea;

1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (pyrimidin-5-yl Urea;

4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) ureido) benzamide;

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazine-2 -Yl) phenyl) ureido) benzamide;

N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5- Triazin-2-yl) phenyl) ureido) benzamide;

N-(2-(메틸아미노)에틸)-4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (methylamino) ethyl) -4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazine-2 -Yl) phenyl) ureido) benzamide;

N-메틸-N-(2-(메틸아미노)에틸)-4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N-methyl-N- (2- (methylamino) ethyl) -4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5- Triazin-2-yl) phenyl) ureido) benzamide;

1-(4-((R)-3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;1- (4-((R) -3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydrofuran-3-yljade C) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (4- (piperazin- 1-carbonyl) phenyl) urea;

1-(4-(4-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5 -Triazin-2-yl) phenyl) urea;

1-(4-(4-에틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-ethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5 -Triazin-2-yl) phenyl) urea;

1-(4-(4-이소프로필피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3, 5-triazin-2-yl) phenyl) urea;

1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (pyridin-4-yl) urea;

1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (pyridin-3-yl) urea;

1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (pyridazin-4-yl) urea;

1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (pyrimidin-5-yl) urea;

4-(3-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;4- (3- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) Phenyl) ureido) benzamide;

1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydro Furan-3-yloxy) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (4- (piperazin-1-carbonyl) phenyl) urea;

1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-에틸피페라진-1-카르보닐)페닐)-3-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-ethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3- Yloxy) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-이소프로필피페라진-1-카르보닐)페닐)-3-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3 -Yloxy) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine-3- Urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridazine-4 -Yl) urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyrimidine-5 -Yl) urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine-4- Urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenylurea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-클로로페닐)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4-chlorophenyl Urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-플루오로페닐)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4-fluoro Phenyl) urea;

메틸 4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조에이트;Methyl 4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzo Eight;

4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산;4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid;

4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)벤즈아미드;4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N -(2- (dimethylamino) ethyl) benzamide;

4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)-N-메틸벤즈아미드;4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N -(2- (dimethylamino) ethyl) -N-methylbenzamide;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3 -(Dimethylamino) pyrrolidine-1-carbonyl) phenyl) urea;

4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzamide ;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (pipe Razin-1-carbonyl) phenyl) urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4 Ethylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4 Isopropylpiperazine-1-carbonyl) phenyl) urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4 -(Dimethylamino) piperidine-1-carbonyl) phenyl) urea;

1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (4-methyl-1,4-diazepan-1-yl) -6 Morpholino-1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (piperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-n-프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-n-propylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (4-methyl-1,4-diazepan-1-yl) -6 Morpholino-1,3,5-triazin-2-yl) phenyl) urea;

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (4-methyl-1,4-diazepan-1-yl) -6-morpholino-1,3, 5-triazin-2-yl) phenyl) ureido) benzamide;

N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (4-methyl-1,4-diazepan-1-yl) -6-morpholino- 1,3,5-triazin-2-yl) phenyl) ureido) benzamide;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenyl Urea;

1-(4-클로로페닐)-3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-chlorophenyl) -3- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine-2 -Yl) phenyl) urea;

1-(4-플루오로페닐)-3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-fluorophenyl) -3- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine- 2-yl) phenyl) urea;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-3-yl) urea;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-4-yl) urea;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridazin-4-yl) urea;

1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyrimidin-5-yl) urea;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (piperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-n-프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-n-propylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (4-ethyl-1,4-diazepan-1-yl) -6 Morpholino-1,3,5-triazin-2-yl) phenyl) urea;

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (4-ethyl-1,4-diazepan-1-yl) -6-morpholino-1,3, 5-triazin-2-yl) phenyl) ureido) benzamide;

N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (4-ethyl-1,4-diazepan-1-yl) -6-morpholino- 1,3,5-triazin-2-yl) phenyl) ureido) benzamide;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenyl Urea;

1-(4-클로로페닐)-3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-chlorophenyl) -3- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine-2 -Yl) phenyl) urea;

1-(4-플루오로페닐)-3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-fluorophenyl) -3- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine- 2-yl) phenyl) urea;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-3-yl) urea;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-4-yl) urea;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridazin-4-yl) urea;

1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyrimidin-5-yl) urea;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (piperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-n-프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-n-propylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (4-propyl-1,4-diazepan-1-yl) -6 Morpholino-1,3,5-triazin-2-yl) phenyl) urea;

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (4-propyl-1,4-diazepan-1-yl) -6-morpholino-1,3, 5-triazin-2-yl) phenyl) ureido) benzamide;

N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (4-propyl-1,4-diazepan-1-yl) -6-morpholino- 1,3,5-triazin-2-yl) phenyl) ureido) benzamide;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenyl Urea;

1-(4-클로로페닐)-3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-chlorophenyl) -3- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine-2 -Yl) phenyl) urea;

1-(4-플루오로페닐)-3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-fluorophenyl) -3- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine- 2-yl) phenyl) urea;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-3-yl) urea;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-4-yl) urea;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridazin-4-yl) urea;

1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyrimidin-5-yl) urea;

1-(4-(4-(4-이소프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4- (4-isopropyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (Pyridin-3-yl) urea;

1-(4-(4-(4-이소프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (4-isopropyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (Pyridin-4-yl) urea;

1-(4-(4-(4-이소프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (4-isopropyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (Pyridazin-4-yl) urea;

1-(4-(4-(4-이소프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (4-isopropyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (Pyrimidin-5-yl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-3-yl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-4-yl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridazin-4-yl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyrimidin-5-yl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenyl Urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-클로로페닐)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4-chlorophenyl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-플루오로페닐)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4-fluorophenyl) urea;

메틸-4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조에이트;Methyl-4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl ) Ureido) benzoate;

4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산;4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urei Benzoic acid;

4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)벤즈아미드;4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urei Fig.)-N- (2- (dimethylamino) ethyl) benzamide;

4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)-N-메틸벤즈아미드;4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urei Fig.)-N- (2- (dimethylamino) ethyl) -N-methylbenzamide;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) urea;

4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urei Benzamide;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-n-프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-n-propylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (piperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레아;1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) urea;

1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(4- (piperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-에틸피페라진-1-카르보닐)페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-ethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-mor Polyno-1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -Phenylurea;

1-(4-클로로페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-chlorophenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazine -2-yl) phenyl) urea;

1-(4-플루오로페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-fluorophenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-tri Azin-2-yl) phenyl) urea;

1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(Pyridin-4-yl) urea;

1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(Pyridazin-4-yl) urea;

1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(Pyridin-3-yl) urea;

1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(Pyrimidin-5-yl) urea;

tert-부틸 4-(4-(4-(3-(4-(메톡시카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복실레이트;tert-butyl 4- (4- (4- (3- (4- (methoxycarbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazin-2-yl) -1,4-diazepan-1-carboxylate;

메틸 4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조에이트;Methyl 4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzo Eight;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenylurea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-클로로페닐)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4-chlorophenyl Urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-플루오로페닐)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4-fluoro Phenyl) urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine-3- Urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine-4- Urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridazine-4 -Yl) urea;

1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyrimidine-5 -Yl) urea;

N-메틸-4-(4-모르폴리노-6-(4-(3-페닐우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드 (M+H) 532.2;N-methyl-4- (4-morpholino-6- (4- (3-phenylureido) phenyl) -1,3,5-triazin-2-yl) -1,4-diazepane-1 -Carboxamide (M + H) 532.2;

4-(4-(4-(3-(4-클로로페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4-chlorophenyl) ureido) phenyl) -6-morpholino-1,3,5-triazin-2-yl) -N-methyl-1,4 Diazephan-1-carboxamide;

4-(4-(4-(3-(4-플루오로페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4-fluorophenyl) ureido) phenyl) -6-morpholino-1,3,5-triazin-2-yl) -N-methyl-1, 4-diazepan-1-carboxamide;

4-(4-(4-(3-(4-(2-(디메틸아미노)에틸카르바모일)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4- (2- (dimethylamino) ethylcarbamoyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazine-2 -Yl) -N-methyl-1,4-diazepane-1-carboxamide;

4-(4-(4-(3-(4-((2-(디메틸아미노)에틸)(메틸)카르바모일)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4-((2- (dimethylamino) ethyl) (methyl) carbamoyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5 -Triazin-2-yl) -N-methyl-1,4-diazepane-1-carboxamide;

4-(4-(4-(3-(4-카르바모일페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4-carbamoylphenyl) ureido) phenyl) -6-morpholino-1,3,5-triazin-2-yl) -N-methyl-1 , 4-diazepan-1-carboxamide;

4-(4-(4-(3-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5- Triazin-2-yl) -N-methyl-1,4-diazepane-1-carboxamide;

N-메틸-4-(4-모르폴리노-6-(4-(3-(4-(피페라진-1-카르보닐)페닐)우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;N-methyl-4- (4-morpholino-6- (4- (3- (4- (piperazin-1-carbonyl) phenyl) ureido) phenyl) -1,3,5-triazine- 2-yl) -1,4-diazepane-1-carboxamide;

N-메틸-4-(4-(4-(3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;N-methyl-4- (4- (4- (3- (4- (4-methylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5- Triazin-2-yl) -1,4-diazepane-1-carboxamide;

4-(4-(4-(3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4- (4-ethylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazine-2 -Yl) -N-methyl-1,4-diazepane-1-carboxamide;

4-(4-(4-(3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazine- 2-yl) -N-methyl-1,4-diazepane-1-carboxamide;

4-(4-(4-(3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5- Triazin-2-yl) -N-methyl-1,4-diazepane-1-carboxamide;

4-(4-(4-(3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-이소프로필-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5- Triazin-2-yl) -N-isopropyl-1,4-diazepane-1-carboxamide;

N-이소프로필-4-(4-(4-(3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;N-isopropyl-4- (4- (4- (3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3, 5-triazin-2-yl) -1,4-diazepane-1-carboxamide;

4-(4-(4-(3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-이소프로필-1,4-디아제판-1-카르복스아미드;4- (4- (4- (3- (4- (4-ethylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazine-2 -Yl) -N-isopropyl-1,4-diazepane-1-carboxamide;

N-이소프로필-4-(4-(4-(3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;N-isopropyl-4- (4- (4- (3- (4- (4-methylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5 -Triazin-2-yl) -1,4-diazepane-1-carboxamide;

N-이소프로필-4-(4-모르폴리노-6-(4-(3-(4-(피페라진-1-카르보닐)페닐)우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;N-isopropyl-4- (4-morpholino-6- (4- (3- (4- (piperazin-1-carbonyl) phenyl) ureido) phenyl) -1,3,5-triazine -2-yl) -1,4-diazepane-1-carboxamide;

N-이소프로필-4-(4-모르폴리노-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;N-isopropyl-4- (4-morpholino-6- (4- (3-pyridin-4-ylureido) phenyl) -1,3,5-triazin-2-yl) -1,4 Diazephan-1-carboxamide;

N-이소프로필-4-(4-모르폴리노-6-(4-(3-피리다진-4-일우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;N-isopropyl-4- (4-morpholino-6- (4- (3-pyridazin-4-ylureido) phenyl) -1,3,5-triazin-2-yl) -1, 4-diazepan-1-carboxamide;

N-이소프로필-4-(4-모르폴리노-6-(4-(3-피리미딘-5-일우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;N-isopropyl-4- (4-morpholino-6- (4- (3-pyrimidin-5-ylureido) phenyl) -1,3,5-triazin-2-yl) -1, 4-diazepan-1-carboxamide;

N-이소프로필-4-(4-모르폴리노-6-(4-(3-피리딘-3-일우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;N-isopropyl-4- (4-morpholino-6- (4- (3-pyridin-3-ylureido) phenyl) -1,3,5-triazin-2-yl) -1,4 Diazephan-1-carboxamide;

1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-3-yl) Urea;

1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) Urea;

1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridazin-4-yl Urea;

1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyrimidin-5-yl Urea;

1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3-phenylurea;

1-(4-클로로페닐)-3-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4-chlorophenyl) -3- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) urea ;

1-(4-플루오로페닐)-3-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4-fluorophenyl) -3- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) Urea;

1-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenylurea;

1-(4-클로로페닐)-3-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-chlorophenyl) -3- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl ) Phenyl) urea;

1-(4-플루오로페닐)-3-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-fluorophenyl) -3- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazine-2- Yl) phenyl) urea;

1-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine- 4-yl) urea;

1-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridazine -4-yl) urea;

1-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyrimidine -5-yl) urea;

1-(4-아세틸페닐)-3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;1- (4-acetylphenyl) -3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-일)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (piperazin-1 -Yl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)아세틸)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2- (dimethyl Amino) acetyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-모르폴리노아세틸)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-morpholi Noacetyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-히드록시아세틸)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-hydroxy Acetyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(메톡시메틸)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (methoxymethyl) Phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-메톡시에틸)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-methoxy Ethyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(1-히드록시에틸)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (1-hydroxy Ethyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-히드록시프로판-2-일)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-hydroxy Propan-2-yl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-히드록시프로필)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-hydroxy Propyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-히드록시-2-메틸프로필)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-hydroxy -2-methylpropyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethyl Amino) piperidine-1-carbonyl) phenyl) urea;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-시아노페닐)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4-cyanophenyl) urea ;

4-(3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드;4- (3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) ureido) -N-methylbenz amides;

4-(3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레이도)-N,N-디메틸벤즈아미드;4- (3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) ureido) -N, N- Dimethylbenzamide;

4-(3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;4- (3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) ureido) benzamide;

1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-카르보닐)피리딘-3-일)우레아;1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (6- (4-methylpipepe Razin-1-carbonyl) pyridin-3-yl) urea;

(R)-1-(4-((디메틸아미노)메틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4-((dimethylamino) methyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (pyridin-4-yl) urea;

(R)-1-(4-아세틸페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4-acetylphenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5 -Triazin-2-yl) phenyl) urea;

(R)-1-(4-(2-(디메틸아미노)아세틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (2- (dimethylamino) acetyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4- Yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-모르폴리노아세틸)페닐)우레아;(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4- (2-morpholinoacetyl) phenyl) urea;

(R)-1-(4-(2-히드록시아세틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (2-hydroxyacetyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(메톡시메틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (methoxymethyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(2-메톡시에틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (2-methoxyethyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(1-히드록시에틸)페닐)-3-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (1-hydroxyethyl) phenyl) -3- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(2-히드록시프로판-2-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (2-hydroxypropan-2-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran- 4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(2-히드록시프로필)페닐)-3-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (2-hydroxypropyl) phenyl) -3- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(2-히드록시-2-메틸프로필)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (2-hydroxy-2-methylpropyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran- 4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro -2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;

(R)-1-(4-시아노페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;(R) -1- (4-cyanophenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3, 5-triazin-2-yl) phenyl) urea;

(R)-N-메틸-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;(R) -N-methyl-4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-tri Azin-2-yl) phenyl) ureido) benzamide;

(R)-N,N-디메틸-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;(R) -N, N-dimethyl-4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5 -Triazin-2-yl) phenyl) ureido) benzamide;

(R)-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;(R) -4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine-2- Yl) phenyl) ureido) benzamide;

(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-카르보닐)피리딘-3-일)우레아;(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (6- (4-methylpiperazin-1-carbonyl) pyridin-3-yl) urea;

1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyrimidine -5-yl) urea;

1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine- 3-yl) urea;

1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine- 4-yl) urea;

1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridazine -4-yl) urea;

1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenylurea;

1-(4-클로로페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-chlorophenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl ) Phenyl) urea;

1-(4-플루오로페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4-fluorophenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazine-2- Yl) phenyl) urea;

메틸 4-(3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조에이트;Methyl 4- (3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido ) Benzoate;

4-(3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산;4- (3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) Benzoic acid;

4-(3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;4- (3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) Benzamide;

1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-mor Polyno-1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (Piperazin-1-carbonyl) phenyl) urea;

1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;

1-(4-(4-에틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-ethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1 , 3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-이소프로필피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino- 1,3,5-triazin-2-yl) phenyl) urea;

1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-mor Polyno-1,3,5-triazin-2-yl) phenyl) urea;

1-{4-[(4-부틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;1- {4-[(4-butylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4- [4- (1-methylethyl) -1,4-diazepane-1- Il] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;

1-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;1- (4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholin-4-yl-1,3,5-triazine-2- Il} phenyl) -3- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;

1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4- [4- (1-methylethyl) -1,4-diazepane-1- Il] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;

1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4- Yl) -1,3,5-triazin-2-yl] phenyl} urea;

1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;

1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;

1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H -Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;

N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1, 3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide;

1-{4-[4-(아제티딘-3-일옥시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;1- {4- [4- (azetidin-3-yloxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-yl Urea;

N-(1-메틸에틸)-3-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]아제티딘-1-카르복스아미드;N- (1-methylethyl) -3-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-tri Azin-2-yl) oxy] azetidine-1-carboxamide;

N-{1-[(4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}페닐)카르보닐]피페리딘-4-일}아세트아미드;N- {1-[(4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} phenyl) carbonyl] piperidin-4-yl} acetamide;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸에틸)-1,4-디아제판-1-일]카르보닐}페닐)우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (1-methylethyl) -1,4-diazepan-1-yl] carbonyl} phenyl) urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-[4-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일카르보닐)페닐]우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- [4- (3 Oxa-8-azabicyclo [3.2.1] oct-8-ylcarbonyl) phenyl] urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-시아노피페리딘-1-일)카르보닐]페닐}우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-cyanopiperidin-1-yl) carbonyl] phenyl} urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ (3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) urea;

1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)우레아;1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ (3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) urea;

1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;

1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;

1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-{4-[(2-메틸피페라진-1-일)카르보닐]페닐}우레아;1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- {4-[(2-methylpiperazin-1 -Yl) carbonyl] phenyl} urea;

1-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)-3-[4-(피페라진-1-일카르보닐)페닐]우레아;1- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazine -2-yl} phenyl) -3- [4- (piperazin-1-ylcarbonyl) phenyl] urea;

1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;

1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-{4-[(3,3,4-트리메틸피페라진-1-일)카르보닐]페닐}우레아;1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- {4-[(3,3,4-trimethyl Piperazin-1-yl) carbonyl] phenyl} urea;

1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-(4-{[(3R)-3-메틸피페라진-1-일]카르보닐}페닐)우레아;1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- (4-{[(3R) -3-methyl Piperazin-1-yl] carbonyl} phenyl) urea;

1-(4-{[(3R)-3,4-디메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[(3R) -3,4-dimethylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4,6-di (morpholin-4-yl) -1 , 3,5-triazin-2-yl] phenyl} urea;

1-(4-{[(3R)-4-시클로부틸-3-메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[(3R) -4-cyclobutyl-3-methylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4,6-di (morpholin-4-yl ) -1,3,5-triazin-2-yl] phenyl} urea;

1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-(4-{[(3R)-3-메틸-4-(프로판-2-일)피페라진-1-일]카르보닐}페닐)우레아;1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- (4-{[(3R) -3-methyl -4- (propan-2-yl) piperazin-1-yl] carbonyl} phenyl) urea;

1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-(4-{[(3S)-3-메틸피페라진-1-일]카르보닐}페닐)우레아;1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- (4-{[(3S) -3-methyl Piperazin-1-yl] carbonyl} phenyl) urea;

N-[2-(디메틸아미노)에틸]-N-메틸-4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6- [4- (propane- 2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1 , 3,5-triazin-2-yl} phenyl) -3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;

1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- (4- {4-[(3S) -3-methylmorpholine- 4-yl] -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;

N-[3-(디메틸아미노)프로필]-4-{[(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [3- (dimethylamino) propyl] -4-{[(4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepane -1-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

N-[2-(디메틸아미노)에틸]-N-메틸-4-{[(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- [2- (dimethylamino) ethyl] -N-methyl-4-{[(4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1, 4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

1-[4-(모르폴린-4-일카르보닐)페닐]-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;1- [4- (morpholin-4-ylcarbonyl) phenyl] -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1, 4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;

N-(2-메톡시에틸)-4-{[(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;N- (2-methoxyethyl) -4-{[(4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepane-1 -Yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;

1-[4-(1,4-디아제판-1-일카르보닐)페닐]-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;1- [4- (1,4-diazepane-1-ylcarbonyl) phenyl] -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl ) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;

1-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(프로판-2-일)-1,4-디아제판-1-일]카르보닐}페닐)우레아;1- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazine -2-yl} phenyl) -3- (4-{[4- (propan-2-yl) -1,4-diazepan-1-yl] carbonyl} phenyl) urea;

1-(4-{[(3S)-4-시클로부틸-3-메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[(3S) -4-cyclobutyl-3-methylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4,6-di (morpholin-4-yl ) -1,3,5-triazin-2-yl] phenyl} urea;

1-(4-{[(3S)-3,4-디메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[(3S) -3,4-dimethylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4,6-di (morpholin-4-yl) -1 , 3,5-triazin-2-yl] phenyl} urea;

1-{4-[4-(모르폴린-4-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}-3-{4-[(3,3,4-트리메틸피페라진-1-일)카르보닐]페닐}우레아;1- {4- [4- (morpholin-4-yl) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- {4-[(3,3,4-trimethylpiperazin-1-yl) carbonyl] phenyl} urea;

1-(4-{[(3S)-3,4-디메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4-(모르폴린-4-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[(3S) -3,4-dimethylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4- (morpholin-4-yl) -6- (tetra Hydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;

1-(4-{[(3S)-3-메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4-(모르폴린-4-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;1- (4-{[(3S) -3-methylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4- (morpholin-4-yl) -6- (tetrahydro- 2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;

1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아; 및1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetra Hydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea; And

1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아. 1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetra Hydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea.

본 발명은 또한 화학식 I의 화합물 및 제약상 허용되는 담체를 포함하는 제약 조성물을 포함한다. 본 발명은 제약상 허용되는 전구약물, 수화된 염, 예컨대 제약상 허용되는 염 또는 그의 혼합물로서 제공될 때 화학식 I의 화합물을 포함한다. The present invention also includes pharmaceutical compositions comprising a compound of formula (I) and a pharmaceutically acceptable carrier. The present invention includes compounds of formula (I) when provided as pharmaceutically acceptable prodrugs, hydrated salts such as pharmaceutically acceptable salts or mixtures thereof.

다른 측면에서, 본 발명은 경구 투여 및 조성물에 적합한 제약상 허용되는 담체가 경구 투여 형태를 포함하는 것을 제공한다. In another aspect, the invention provides that a pharmaceutically acceptable carrier suitable for oral administration and compositions comprises an oral dosage form.

다른 측면에서, 본 발명은 화학식 I의 화합물, 토포이소머라제 I 억제제, MEK 1/2 억제제, HSP90 억제제, 프로카르바진, 다카르바진, 겜시타빈, 카페시타빈, 메토트렉세이트, 탁솔, 탁소테레, 머캅토퓨린, 티오구아닌, 히드록시우레아, 시타라빈, 시클로포스파미드, 이포스파미드, 니트로소우레아, 시스플라틴, 카르보플라틴, 미토마이신, 다카르바진, 프로카르비진, 에토포시드, 테니포시드, 캄파테신, 블레오마이신, 독소루비신, 이다루비신, 다우노루비신, 닥티노마이신, 플리카마이신, 미톡산트론, L-아스파라기나제, 독소루비신, 에피루비신, 5-플루오로우라실, 도세탁셀, 파클리탁셀, 류코보린, 레바미솔, 이리노테칸, 에스트라무스틴, 에토포시드, 질소 머스타드, BCNU, 카르무스틴, 로무스틴, 빈블라스틴, 빈크리스틴, 비노렐빈, 시스플라틴, 카르보플라틴, 옥살리플라틴, 이마티닙 메실레이트, 아바스틴 (베바시주맙), 헥사메틸멜라민, 토포테칸, 티로신 키나제 억제제, 티르포스틴, 헤르비마이신 A, 제니스테인, 에르브스타틴, 히드록시진, 글라티라머 아세테이트, 인터페론 베타-1a, 인터페론 베타-1b, 나탈리주맙 및 라벤두스틴 A로 이루어진 군으로부터 선택된 제2 화합물; 및 제약상 허용되는 담체를 포함하는 조성물을 제공한다. In another aspect, the invention provides compounds of formula I, topoisomerase I inhibitors, MEK 1/2 inhibitors, HSP90 inhibitors, procarbazine, dacarbazine, gemcitabine, capecitabine, methotrexate, taxol, taxotere, mer Captopurine, thioguanine, hydroxyurea, cytarabine, cyclophosphamide, isophosphamide, nitrosourea, cisplatin, carboplatin, mitomycin, dacarbazine, procarbazine, etoposide, teniposide, Camppatesine, bleomycin, doxorubicin, idarubicin, daunorubicin, dactinomycin, plicamycin, mitoxantrone, L-asparaginase, doxorubicin, epirubicin, 5-fluorouracil, docetaxel, paclitaxel, Leucovorin, levamisol, irinotecan, esturamustine, etoposide, nitrogen mustard, BCNU, carmustine, lomustine, vinblastine, vincristine, vinorelbine, cisplatin, carboplatin, Saliplatin, imatinib mesylate, avastin (bevacizumab), hexamethylmelamine, topotecan, tyrosine kinase inhibitor, tyrphostin, herbimycin A, genistein, erbstatin, hydroxyzine, glatiramer acetate, A second compound selected from the group consisting of interferon beta-1a, interferon beta-1b, natalizumab and ravendustin A; And a pharmaceutically acceptable carrier.

다른 측면에서, 제2 화합물은 아바스틴이다. In another aspect, the second compound is avastin.

다른 측면에서, 본 발명은 PI3K-관련 장애의 치료에 효과적인 양의 화학식 I의 화합물을 PI3K-관련 장애의 치료가 필요한 포유동물에게 투여하는 것을 포함하는, 상기 PI3K-관련 장애를 치료하는 방법을 제공한다. In another aspect, the present invention provides a method of treating a PI3K-related disorder, comprising administering to a mammal in need thereof an amount of a compound of Formula (I) effective for the treatment of a PI3K-related disorder. do.

다른 측면에서, PI3K-관련 장애는 재협착, 아테롬성동맥경화증, 골 장애, 관절염, 당뇨병성 망막병증, 건선, 양성 전립선 비대증, 아테롬성동맥경화증, 염증, 혈관신생, 면역 장애, 췌장염, 신장 질환 및 암으로부터 선택된다. In other aspects, PI3K-related disorders include restenosis, atherosclerosis, bone disorders, arthritis, diabetic retinopathy, psoriasis, benign prostatic hyperplasia, atherosclerosis, inflammation, angiogenesis, immune disorders, pancreatitis, kidney disease and cancer Is selected from.

다른 측면에서, PI3K-관련 장애는 암이다. In another aspect, the PI3K-related disorder is cancer.

다른 측면에서, 암은 백혈병, 피부암, 방광암, 유방암, 자궁암, 난소암, 전립선암, 폐암, 결장암, 췌장암, 신장암, 위암 및 뇌암으로 이루어진 군으로부터 선택된다. In another aspect, the cancer is selected from the group consisting of leukemia, skin cancer, bladder cancer, breast cancer, uterine cancer, ovarian cancer, prostate cancer, lung cancer, colon cancer, pancreatic cancer, kidney cancer, gastric cancer and brain cancer.

다른 측면에서, 본 발명은 mTOR-관련 장애의 치료에 효과적인 양의 화학식 I의 화합물을 mTOR-관련 장애의 치료가 필요한 포유동물에게 투여하는 것을 포함하는, 상기 mTOR-관련 장애를 치료하는 방법을 제공한다. In another aspect, the present invention provides a method of treating an mTOR-related disorder comprising administering to a mammal in need thereof an amount of a compound of Formula I effective in the treatment of the mTOR-associated disorder. do.

다른 측면에서, mTOR-관련 장애는 재협착, 아테롬성동맥경화증, 골 장애, 관절염, 당뇨병성 망막병증, 건선, 양성 전립선 비대증, 아테롬성동맥경화증, 염증, 혈관신생, 면역 장애, 췌장염, 신장 질환 및 암으로부터 선택된다. In other aspects, mTOR-related disorders include restenosis, atherosclerosis, bone disorders, arthritis, diabetic retinopathy, psoriasis, benign prostatic hyperplasia, atherosclerosis, inflammation, angiogenesis, immune disorders, pancreatitis, kidney disease and cancer Is selected from.

다른 측면에서, mTOR-관련 장애는 암이다. In another aspect, the mTOR-related disorder is cancer.

다른 측면에서, 암은 백혈병, 피부암, 방광암, 유방암, 자궁암, 난소암, 전립선암, 폐암, 결장암, 췌장암, 신장암, 위암 및 뇌암으로 이루어진 군으로부터 선택된다. In another aspect, the cancer is selected from the group consisting of leukemia, skin cancer, bladder cancer, breast cancer, uterine cancer, ovarian cancer, prostate cancer, lung cancer, colon cancer, pancreatic cancer, kidney cancer, gastric cancer and brain cancer.

다른 측면에서, 본 발명은 hSMG-1-관련 장애의 치료에 효과적인 양의 화학식 I의 화합물을 hSMG-1-관련 장애의 치료가 필요한 포유동물에게 투여하는 것을 포함하는, 상기 hSMG-1-관련 장애를 치료하는 방법을 제공한다. In another aspect, the present invention comprises administering to a mammal in need thereof an amount of a compound of formula (I) effective in the treatment of an hSMG-1-related disorder. It provides a way to treat it.

다른 측면에서, hSMG-1-관련 장애는 재협착, 아테롬성동맥경화증, 골 장애, 관절염, 당뇨병성 망막병증, 건선, 양성 전립선 비대증, 아테롬성동맥경화증, 염증, 혈관신생, 면역 장애, 췌장염, 신장 질환 및 암으로부터 선택된다. In another aspect, hSMG-1-related disorders include restenosis, atherosclerosis, bone disorders, arthritis, diabetic retinopathy, psoriasis, benign prostatic hyperplasia, atherosclerosis, inflammation, angiogenesis, immune disorders, pancreatitis, kidney disease And cancer.

다른 측면에서, hSMG-1-관련 장애는 암이다. In another aspect, the hSMG-1-related disorder is cancer.

다른 측면에서, 암은 백혈병, 피부암, 방광암, 유방암, 자궁암, 난소암, 전립선암, 폐암, 결장암, 췌장암, 신장암, 위암 및 뇌암으로 이루어진 군로부터 선택된다. In another aspect, the cancer is selected from the group consisting of leukemia, skin cancer, bladder cancer, breast cancer, uterine cancer, ovarian cancer, prostate cancer, lung cancer, colon cancer, pancreatic cancer, kidney cancer, gastric cancer and brain cancer.

다른 측면에서, 본 발명은 진행성 신세포 암종의 치료에 효과적인 양의 화학식 I의 화합물을 진행성 신세포 암종의 치료가 필요한 포유동물에게 투여하는 것을 포함하는, 상기 진행성 신세포 암종을 치료하는 방법을 제공한다. In another aspect, the present invention provides a method of treating advanced renal cell carcinoma comprising administering to a mammal in need thereof an amount of a compound of formula (I) effective for the treatment of advanced renal cell carcinoma. do.

다른 측면에서, 본 발명은 급성 림프모구성 백혈병의 치료에 효과적인 양의 화학식 I의 화합물을 급성 림프모구성 백혈병의 치료가 필요한 포유동물에게 투여하는 것을 포함하는, 상기 급성 림프모구성 백혈병을 치료하는 방법을 제공한다. In another aspect, the present invention provides a method for treating acute lymphoblastic leukemia, comprising administering to a mammal in need thereof an amount of a compound of Formula I effective in the treatment of acute lymphoblastic leukemia. Provide a method.

다른 측면에서, 본 발명은 악성 흑색종의 치료에 효과적인 양의 화학식 I의 화합물을 악성 흑색종의 치료가 필요한 포유동물에게 투여하는 것을 포함하는, 상기 급성 악성 흑색종을 치료하는 방법을 제공한다. In another aspect, the present invention provides a method of treating acute malignant melanoma, comprising administering to a mammal in need of such treatment an amount of a compound of formula (I) effective in treating malignant melanoma.

다른 측면에서, 본 발명은 연조직 또는 골 육종의 치료에 효과적인 양의 화학식 I의 화합물을 연조직 또는 골 육종의 치료가 필요한 포유동물에게 투여하는 것을 포함하는, 상기 연조직 또는 골 육종을 치료하는 방법을 제공한다. In another aspect, the present invention provides a method of treating soft tissues or bone sarcomas comprising administering to a mammal in need thereof a therapeutic amount of a compound of formula (I) in the treatment of soft tissues or bone sarcomas. do.

다른 측면에서, 본 발명은 암 치료에 효과적인 양의 화학식 I의 화합물; 토포이소머라제 I 억제제, MEK 1/2 억제제, HSP90 억제제, 프로카르바진, 다카르바진, In another aspect, the invention provides an amount of a compound of formula I in an effective amount for treating cancer; Topoisomerase I inhibitors, MEK 1/2 inhibitors, HSP90 inhibitors, procarbazine, dacarbazine,

Figure 112010076169004-pct00012
Figure 112010076169004-pct00012

겜시타빈, 카페시타빈, 메토트렉세이트, 탁솔, 탁소테레, 머캅토퓨린, 티오구아닌, 히드록시우레아, 시타라빈, 시클로포스파미드, 이포스파미드, 니트로소우레아, 시스플라틴, 카르보플라틴, 미토마이신, 다카르바진, 프로카르비진, 에토포시드, 테니포시드, 캄파테신, 블레오마이신, 독소루비신, 이다루비신, 다우노루비신, 닥티노마이신, 플리카마이신, 미톡산트론, L-아스파라기나제, 독소루비신, 에피루비신, 5-플루오로우라실, 도세탁셀, 파클리탁셀, 류코보린, 레바미솔, 이리노테칸, 에스트라무스틴, 에토포시드, 질소 머스타드, BCNU, 카르무스틴, 로무스틴, 빈블라스틴, 빈크리스틴, 비노렐빈, 시스플라틴, 카르보플라틴, 옥살리플라틴, 이마티닙 메실레이트, 아바스틴 (베바시주맙), 헥사메틸멜라민, 토포테칸, 티로신 키나제 억제제, 티르포스틴, 헤르비마이신 A, 제니스테인, 에르브스타틴 및 라벤두스틴 A로 이루어진 군로부터 선택된 제2 화합물; 및 제약상 허용되는 담체를 포함하는 조성물을 백혈병, 피부암, 방광암, 유방암, 자궁암, 난소암, 전립선암, 폐암, 결장암, 췌장암, 신장암, 위암 및 뇌암으로 이루어진 군로부터 선택된 암의 치료가 필요한 포유동물에게 투여하는 것을 포함하는, 상기 백혈병, 피부암, 방광암, 유방암, 자궁암, 난소암, 전립선암, 폐암, 결장암, 췌장암, 신장암, 위암 및 뇌암으로 이루어진 군로부터 선택된 암을 치료하는 방법을 제공한다. Gemcitabine, capecitabine, methotrexate, taxol, taxotere, mercaptopurine, thioguanine, hydroxyurea, cytarabine, cyclophosphamide, iphosphamide, nitrosourea, cisplatin, carboplatin, mitomycin, Dacarbazine, procarbazine, etoposide, teniposide, campatin, bleomycin, doxorubicin, idarubicin, daunorubicin, dactinomycin, plicamycin, mitoxantrone, L-asparaginase, doxorubicin , Epirubicin, 5-fluorouracil, docetaxel, paclitaxel, leucovorin, levamisol, irinotecan, esturamustine, etoposide, nitrogen mustard, BCNU, carmustine, lomustine, vinblastine, vincristine, Vinorelbine, cisplatin, carboplatin, oxaliplatin, imatinib mesylate, avastin (bevacizumab), hexamethylmelamine, topotecan, tyrosine kinase inhibitors, typhostin, he A second compound selected from the non-erythromycin A, genistein, Er and La probe statin group consisting bendu sustaining A; And a pharmaceutically acceptable carrier comprising: a mammal in need of treatment for a cancer selected from the group consisting of leukemia, skin cancer, bladder cancer, breast cancer, uterine cancer, ovarian cancer, prostate cancer, lung cancer, colon cancer, pancreatic cancer, kidney cancer, gastric cancer and brain cancer Provided are methods for treating cancer selected from the group consisting of leukemia, skin cancer, bladder cancer, breast cancer, uterine cancer, ovarian cancer, prostate cancer, lung cancer, colon cancer, pancreatic cancer, kidney cancer, stomach cancer and brain cancer, comprising administering to an animal. .

다른 측면에서, 본 발명은 mTOR의 억제에 효과적인 양의 화학식 I의 화합물을 mTOR의 억제가 필요한 대상체에게 투여하는 것을 포함하는, 상기 대상체에서 mTOR을 억제하는 방법을 제공한다. In another aspect, the present invention provides a method of inhibiting mTOR in a subject comprising administering to a subject in need thereof an amount of a compound of Formula (I) effective to inhibit mTOR.

다른 측면에서, 본 발명은 PI3K의 억제에 효과적인 양의 화학식 I의 화합물을 PI3K의 억제가 필요한 대상체에게 투여하는 것을 포함하는, 상기 대상체에서 PI3K를 억제하는 방법을 제공한다. In another aspect, the present invention provides a method of inhibiting PI3K in a subject comprising administering to a subject in need thereof an amount of a compound of Formula (I) effective to inhibit PI3K.

다른 측면에서, 본 발명은 hSMG-1의 억제에 효과적인 양의 화학식 I의 화합물을 hSMG-1의 억제가 필요한 대상체에게 투여하는 것을 포함하는, 상기 대상체에서 hSMG-1을 억제하는 방법을 제공한다. In another aspect, the present invention provides a method of inhibiting hSMG-1 in a subject comprising administering to a subject in need thereof an amount of a compound of Formula (I) effective to inhibit hSMG-1.

다른 측면에서, 본 발명은 mTOR, PI3K 및 hSMG-1의 억제에 효과적인 양의 화학식 I의 화합물을 mTOR, PI3K 및 hSMG-1의 억제가 필요한 대상체에게 투여하는 것을 포함하는, 상기 대상체에서 mTOR, PI3K 및 hSMG-1을 함께 억제하는 방법을 제공한다. In another aspect, the invention comprises administering to a subject in need of inhibition of mTOR, PI3K and hSMG-1 an amount of a compound of Formula (I) effective to inhibit mTOR, PI3K and hSMG-1. And hSMG-1 together.

또다른 측면에서, 본 발명은 다음과 같은 화학식 I의 화합물의 합성 방법을 제공한다:In another aspect, the present invention provides a method for synthesizing a compound of formula I:

상기 방법은 2,4,6-트리클로로[1,3,5]트리아진을

Figure 112010076169004-pct00013
와 반응시켜 중간체 디클로로트리아진 화합물
Figure 112010076169004-pct00014
을 형성하는 단계를 포함한다.This method uses 2,4,6-trichloro [1,3,5] triazine.
Figure 112010076169004-pct00013
Intermediate Dichlorotriazine Compounds by Reaction with
Figure 112010076169004-pct00014
Forming a step.

화학식 I의 화합물의 합성 방법은 추가로 상기 중간체 디클로로트리아진 화합물을

Figure 112010076169004-pct00015
과 반응시켜 중간체 화합물
Figure 112010076169004-pct00016
을 형성하는 것을 포함한다.The process for the synthesis of compounds of formula (I) further comprises the intermediate dichlorotriazine compound
Figure 112010076169004-pct00015
To react with intermediate compounds
Figure 112010076169004-pct00016
It includes forming a.

화학식 I의 화합물의 합성 방법은 추가로 중간체 디클로로트리아진 화합물을

Figure 112010076169004-pct00017
과 반응시켜 중간체 화합물
Figure 112010076169004-pct00018
을 형성하는 것을 포함한다 (여기서, 각각의 R6, R7, R8 및 R9는 독립적으로 선택되고, 화학식 I에 따라 정의됨).The process for the synthesis of compounds of formula (I) further comprises intermediate dichlorotriazine compounds
Figure 112010076169004-pct00017
To react with intermediate compounds
Figure 112010076169004-pct00018
Forming a compound wherein R 6 , R 7 , R 8 and R 9 are each independently selected and defined according to formula (I).

화학식 I의 화합물의 합성 방법에서 반응 잔기

Figure 112010076169004-pct00019
은
Figure 112010076169004-pct00020
이다.Reaction residues in the method for the synthesis of compounds of formula (I)
Figure 112010076169004-pct00019
silver
Figure 112010076169004-pct00020
to be.

본 발명의 화합물을 합성하기 위해 사용된 절차는 반응식 1 내지 12에 기술되고, 실시예에서 설명된다. 기술된 절차의 합리적인 변형은 본 발명의 범주내에 있는 것으로 의도된다:The procedure used to synthesize the compounds of the present invention is described in Schemes 1-12, and described in the Examples. Reasonable variations of the described procedure are intended to be within the scope of the present invention:

<반응식 1><Reaction Scheme 1>

Figure 112010076169004-pct00021
Figure 112010076169004-pct00021

(a) 아세톤/H2O/Et3N/-10℃; (a) acetone / H 2 O / Et 3 N / -10 ° C .;

(b) 4-아미노페닐 보론산/(Ph3)4P(Pd)/Na2CO3/DME/환류 또는 마이크로파; (b) 4-aminophenyl boronic acid / (Ph 3 ) 4 P (Pd) / Na 2 CO 3 / DME / reflux or microwave;

(c) 상응하는 알콜/n-BuLi 또는 NaH/THF/RT 또는 환류;(c) the corresponding alcohol / n-BuLi or NaH / THF / RT or reflux;

(d) R = 알킬 RMgBr/Pd(0)/THF인 경우; R = 알켄 또는 시클로알킬, 또는 1 또는 2개의 헤테로원자를 갖는 시클로알킬인 경우, 변형은 비닐 스탄난/Pd(0)/유기 용매/환류 (스틸 커플링)를 통해 이루어짐; R = 아릴 또는 헤테로아릴인 경우, 변형은 아릴 보로네이트/(Ph3)4P(Pd)/Na2CO3/DME/환류 또는 마이크로파 (스즈키 커플링)을 통해 이루어짐;(d) when R = alkyl RMgBr / Pd (0) / THF; When R = alkene or cycloalkyl, or cycloalkyl having 1 or 2 heteroatoms, the modification is via vinyl stannan / Pd (0) / organic solvent / reflux (steel coupling); If R = aryl or heteroaryl, the modification is via aryl boronate / (Ph 3 ) 4 P (Pd) / Na 2 CO 3 / DME / reflux or microwave (Suzuki coupling);

(e) R3이 -OR5인 경우, DCM/ClCOOR5/Et3N/0℃ 내지 실온; R5가 NHR5인 경우, DMAP/DCM/R5NCO 또는 (COCl2)3/Et3N/R5NH2 (e) when R 3 is -OR 5 , DCM / ClCOOR 5 / Et 3 N / 0 ° C. to room temperature; When R 5 is NHR 5 , DMAP / DCM / R 5 NCO or (COCl 2 ) 3 / Et 3 N / R 5 NH 2

본 발명의 화합물은 반응식 1에 도시된 바와 같은 다단계 순서에 따라 제조한다. 1개의 염소 원자는 한번에 상이한 온도에서 선택적으로 대체하였다. 시판 구입가능한 시아누르산 클로라이드 1을 -10℃에서 모르폴린 또는 치환된 모르폴린 유도체와 반응시켜 모노 모르폴린 유도체 2를 제공하였다. 이 중추적 중간체 2를 상이한 친핵체와 반응시킬 수 있다. 본 발명에서, 중간체 2를 상이한 아민 및 알콜과 반응시켜 각각 화합물 3 및 5를 제공하였다. 중간체 3 및 5에 있는 3번째 염소 원자를 (Ph3)4P(Pd)/Na2CO3/DME/환류 또는 마이크로파 조건 하에 4-아미노아릴 및 아미노헤테로아릴 보론산으로 대체하여 각각 화합물 4 및 8을 수득하였다. 아미노기를 출발 물질의 유용성에 의존적인 상이한 2개의 절차에 따라 우레아 유도체로 전환시킬 수 있다. 본원에 보고된 일부 실시예를 화합물 4 또는 8을 적절하게 치환된 이소시아네이트 유도체와 반응시켜 우레아 유도체로 변형시켰다. 본원에 보고된 다수의 우레아 유도체를 중간체 4 또는 8을 트리포스겐/Et3N 및 적절하게 치환된 1급 아민 유도체와 반응시켜 제조하였다. 상응하는 카르바메이트 유도체를 중간체 4 또는 8을 적절하게 치환된 클로로포르메이트 시약과 반응시켜 제조하였다. 또한, 중간체 2를 사용하여 화학식 6의 유도체 (여기서, R은 알킬, 알켄, 알킨, 아릴 또는 헤테로아릴임)를 제조하였다. 화합물 6을 적절하게 치환된 알킬과 반응시켜 알킬기 또는 시클로알킬기를 중간체 6 또는 시클로알킬 마그네슘 브로마이드 또는 상응하는 적절하게 치환된 유기-아연 시약에 도입시켰다. Pd 촉매화된 적절하게 치환된 비닐 주석 유도체에 의해 알켄을 화합물 6에 도입할 수 있다. 유사하게, 화합물 6을 상응하는 보론산 (스즈키(Suzuki) 커플링) 또는 아릴 또는 헤테로아릴 마그네슘 브로마이드와 반응시켜 아릴 또는 헤테로아릴 치환기를 도입할 수 있다. 화합물 6을 적절하게 치환된 알킨 및 Pd(0)과 반응시켜 알킨을 도입할 수 있다. 도입된 알킨 및 알켄을 다른 유도체, 예컨대 알킬, 알콜 및 아민 잔기 내로 관능적으로 전환시킬 수 있다. 상세한 절차를 제조된 각각의 유도체에 대한 실험 부분에 기재한다.Compounds of the present invention are prepared according to a multi-step sequence as shown in Scheme 1. One chlorine atom was selectively replaced at different temperatures at one time. Commercially available cyanuric acid chloride 1 was reacted with morpholine or substituted morpholine derivatives at −10 ° C. to provide mono morpholine derivative 2. This pivotal intermediate 2 can be reacted with different nucleophiles. In the present invention, intermediate 2 was reacted with different amines and alcohols to give compounds 3 and 5, respectively. Replacing the third chlorine atom in intermediates 3 and 5 with 4-aminoaryl and aminoheteroaryl boronic acid under (Ph 3 ) 4 P (Pd) / Na 2 CO 3 / DME / reflux or microwave conditions to yield Compound 4 and 8 was obtained. The amino groups can be converted to urea derivatives following two different procedures depending on the availability of the starting material. Some examples reported herein were modified to urea derivatives by reacting compounds 4 or 8 with appropriately substituted isocyanate derivatives. Many of the urea derivatives reported herein were prepared by reacting intermediates 4 or 8 with triphosgene / Et 3 N and suitably substituted primary amine derivatives. Corresponding carbamate derivatives were prepared by reacting intermediate 4 or 8 with an appropriately substituted chloroformate reagent. In addition, intermediate 2 was used to prepare derivatives of formula 6 wherein R is alkyl, alkene, alkyne, aryl or heteroaryl. Compound 6 was reacted with suitably substituted alkyl to introduce the alkyl or cycloalkyl group into intermediate 6 or cycloalkyl magnesium bromide or the corresponding suitably substituted organo-zinc reagent. Alkenes can be introduced into compound 6 by Pd catalyzed suitably substituted vinyl tin derivatives. Similarly, compound 6 can be reacted with the corresponding boronic acid (Suzuki coupling) or aryl or heteroaryl magnesium bromide to introduce aryl or heteroaryl substituents. Alkynes can be introduced by reacting compound 6 with suitably substituted alkyne and Pd (0). The alkynes and alkenes introduced can be sensually converted into other derivatives such as alkyl, alcohol and amine residues. Detailed procedures are described in the experimental section for each derivative produced.

<반응식 2><Reaction Scheme 2>

Figure 112010076169004-pct00022
Figure 112010076169004-pct00022

본 발명의 특정 화합물은 반응식 2에서 요약된 방법에 의해 제조하였다. Certain compounds of the present invention were prepared by the method outlined in Scheme 2.

<반응식 3><Reaction Scheme 3>

Figure 112010076169004-pct00023
Figure 112010076169004-pct00023

본 발명의 화합물은 또한 반응식 3에 설명된 방법에 따라 제조하였다. Compounds of the invention were also prepared according to the method described in Scheme 3.

<반응식 4><Reaction Scheme 4>

벤젠-1,4-디아민 중간체는 반응식 4에 나타난 바와 같이 4-플루오로니트로벤젠과 적절한 아민으로부터 제조하였다. Benzene-1,4-diamine intermediates were prepared from 4-fluoronitrobenzene and appropriate amines as shown in Scheme 4.

Figure 112010076169004-pct00024
Figure 112010076169004-pct00024

(a) NHR'R"/톨루엔; (b) H2/탄소상 팔라듐, 에틸 아세테이트, 메탄올.(a) NHR'R "/ toluene; (b) H 2 / palladium on carbon, ethyl acetate, methanol.

주의: R' 또는 R" = H이거나 또는 친핵성 아민을 함유한 경우, 상기 아민은 그의 Boc 유도체로 전환시켰다. 탈보호는 우레아 형성의 최종 단계에 따라 달성하였다.Note: If R 'or R "= H or contains a nucleophilic amine, the amine was converted to its Boc derivative. Deprotection was achieved according to the final stage of urea formation.

<반응식 5><Reaction Scheme 5>

Figure 112010076169004-pct00025
Figure 112010076169004-pct00025

(a) ROH/NaH/톨루엔; (b) H2/탄소상 팔라듐, 에틸 아세테이트, 메탄올.(a) ROH / NaH / toluene; (b) H 2 / palladium on carbon, ethyl acetate, methanol.

주의: R이 친핵성 아민을 함유한 경우, 상기 아민을 그의 Boc 유도체로 전환시켰다. 탈보호는 우레아 형성의 최종 단계에 따라 달성하였다.Note: If R contained a nucleophilic amine, the amine was converted to its Boc derivative. Deprotection was achieved according to the final stage of urea formation.

4-(알콕시)아닐린 중간체는 반응식 5에 나타난 바와 같이 4-플루오로니트로벤젠 및 적절한 알콜로부터 제조하였다. The 4- (alkoxy) aniline intermediate was prepared from 4-fluoronitrobenzene and the appropriate alcohol as shown in Scheme 5.

<반응식 6><Reaction Scheme 6>

Figure 112010076169004-pct00026
Figure 112010076169004-pct00026

(a) Na2CO3, 아세톤, 물; (b) NaHCO3, 아세톤, 물(a) Na 2 CO 3 , acetone, water; (b) NaHCO 3 , acetone, water

(c) SnCl2, 피리딘, DMF; (d) 트리포스겐, Et3N, CH2Cl2, 이어서 RNH2 (c) SnCl 2 , pyridine, DMF; (d) Triphosgen, Et 3 N, CH 2 Cl 2 , then RNH 2

(e) 옥손, 아세토니트릴, 물.(e) oxone, acetonitrile, water.

티오모르폴린 및 비스 모르폴린 화합물은 반응식 6에 나타난 바와 같이 2,4-디클로로-6-(4-니트로페닐)-1,3,5-트리아진 및 적절한 모르폴린 및 티오모르폴린 시약으로부터 제조하였다. Thiomorpholine and bis morpholine compounds were prepared from 2,4-dichloro-6- (4-nitrophenyl) -1,3,5-triazine and appropriate morpholine and thiomorpholine reagents as shown in Scheme 6. .

<반응식 7><Reaction Scheme 7>

Figure 112010076169004-pct00027
Figure 112010076169004-pct00027

(a) Na2CO3, 아세톤, 물; (b) Pd(PPh3)4, 톨루엔(a) Na 2 CO 3 , acetone, water; (b) Pd (PPh 3 ) 4 , toluene

(c) Fe, 아세트산, 에틸 아세테이트, 물(c) Fe, acetic acid, ethyl acetate, water

(d) 트리포스겐, Et3N, CH2Cl2, 이어서 RNH2 (d) Triphosgen, Et 3 N, CH 2 Cl 2 , then RNH 2

(e) H2/Pd-C, 에틸 아세테이트, 메틸렌 클로라이드, 메탄올.(e) H 2 / Pd-C, ethyl acetate, methylene chloride, methanol.

디히드로피란 및 테트라히드로피란 화합물은 반응식 7에 나타난 바와 같이 2,4-디클로로-6-(4-니트로페닐)-1,3,5-트리아진, 트리부틸(3,6-디히드로-2H-피란-4-일)스탄난 및 적절한 모르폴린으로부터 제조하였다. The dihydropyran and tetrahydropyran compounds were prepared as shown in Scheme 7, 2,4-dichloro-6- (4-nitrophenyl) -1,3,5-triazine, tributyl (3,6-dihydro-2H -Pyran-4-yl) stannan and appropriate morpholine.

<반응식 8><Reaction Scheme 8>

Figure 112010076169004-pct00028
Figure 112010076169004-pct00028

(a) NHR'R", Et3N, CH2Cl2 (a) NHR'R ", Et 3 N, CH 2 Cl 2

(b) H2/탄소상 팔라듐, 에틸 아세테이트, 메탄올.(b) H 2 / palladium on carbon, ethyl acetate, methanol.

주의: R1 또는 R2가 친핵성 아민을 함유한 경우, 상기 아민을 그의 Boc 유도체로 전환시켰다. 탈보호는 우레아 형성의 최종 단계에 따라 달성하였다.Caution: If R 1 or R 2 contained a nucleophilic amine, the amine was converted to its Boc derivative. Deprotection was achieved according to the final stage of urea formation.

(4-아미노페닐)(피페라진-1-일)메타논 중간체는 반응식 8에 나타난 바와 같이 4-니트로벤조일 클로라이드 및 적절한 아민으로부터 제조하였다. (4-aminophenyl) (piperazin-1-yl) methanone intermediate was prepared from 4-nitrobenzoyl chloride and appropriate amines as shown in Scheme 8.

<반응식 9><Reaction Scheme 9>

Figure 112010076169004-pct00029
Figure 112010076169004-pct00029

(a) Na2CO3, 아세톤, 물; (b) NaHCO3, 아세톤, 물(a) Na 2 CO 3 , acetone, water; (b) NaHCO 3 , acetone, water

(c) H2-Pd-C, 에틸 아세테이트, 메틸렌 클로라이드, 메탄올(c) H 2 -Pd-C, ethyl acetate, methylene chloride, methanol

(d) 트리포스겐, Et3N, CH2Cl2, 이어서 RNH2 (d) Triphosgen, Et 3 N, CH 2 Cl 2 , then RNH 2

1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-우레아 화합물은 반응식 9에 나타난 바와 같이 2,4-디클로로-6-(4-니트로페닐)-1,3,5-트리아진, (R)-3-메틸모르폴린, 3-옥사-8-아자비시클로[3.2.1]옥탄-히드로클로라이드 및 적절한 아민으로부터 제조하였다. 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1,3,5- The triazin-2-yl) phenyl) -3-urea compound is a 2,4-dichloro-6- (4-nitrophenyl) -1,3,5-triazine, (R) -3 as shown in Scheme 9. Prepared from -methylmorpholine, 3-oxa-8-azabicyclo [3.2.1] octane-hydrochloride and appropriate amines.

<반응식 10><Reaction formula 10>

Figure 112010076169004-pct00030
Figure 112010076169004-pct00030

Figure 112010076169004-pct00031
Figure 112010076169004-pct00031

tert-부틸 1H-피롤-1-카르복실레이트로부터의 tert-부틸 6-히드록시-3-옥사-8-아자비시클로[3.2.1]옥탄-8-카르복실레이트의 (6S') 및 (6R') 이성질체 둘다의 제조는 반응식 10에 나타냈다. (6S ') and (6R) of tert-butyl 6-hydroxy-3-oxa-8-azabicyclo [3.2.1] octane-8-carboxylate from tert-butyl 1H-pyrrole-1-carboxylate The preparation of both isomers is shown in Scheme 10.

<반응식 11><Reaction Scheme 11>

Figure 112010076169004-pct00032
Figure 112010076169004-pct00032

(6S')-tert-부틸 6-아미노-3-옥사-8-아자비시클로[3.2.1]옥탄-8-카르복실레이트 및 (6R')-tert-부틸 6-플루오로-6-(알킬, 아릴 또는 헤테로아릴)-3-옥사-8-아자비시클로[3.2.1]옥탄-8-카르복실레이트 화합물은 반응식 11에 나타난 바와 같이 tert-부틸 6-옥소-3-옥사-8-아자비시클로[3.2.1]옥탄-8-카르복실레이트 (반응식 10) 및 적절한 아민 또는 그리냐르 시약으로부터 제조할 수 있다. (6S ')-tert-butyl 6-amino-3-oxa-8-azabicyclo [3.2.1] octane-8-carboxylate and (6R')-tert-butyl 6-fluoro-6- (alkyl , Aryl or heteroaryl) -3-oxa-8-azabicyclo [3.2.1] octane-8-carboxylate compound is prepared using tert-butyl 6-oxo-3-oxa-8-azabicyclo as shown in Scheme 11. [3.2.1] octane-8-carboxylate (Scheme 10) and appropriate amines or Grignard reagents.

<반응식 12><Reaction Scheme 12>

Figure 112010076169004-pct00033
Figure 112010076169004-pct00033

화학식 I의 화합물은 반응식 12에 나타난 바와 같이 시아누르산 클로라이드로부터 제조할 수 있다. Compounds of formula (I) can be prepared from cyanuric chloride as shown in Scheme 12.

<정의><Definition>

하기의 정의는, 문맥이 달리 나타내지 않는 한, 본 발명의 화합물과 연관되어 사용된다. 일반적으로, 주어진 기에 존재하는 탄소 원자의 갯수는 "Cx-Cy" (여기서, x 및 y는 각각 하한 및 상한임)로 지정된다. 예를 들면, "C1-C6"으로 표시된 기는 1 내지 6개의 탄소 원자를 함유한다. 본원의 정의에 사용된 바와 같은 탄소 갯수는 탄소 백본 및 탄소 분지에 관해 언급하지만, 치환기, 예컨대 알콕시 치환 등의 탄소 원자를 포함하지는 않다. 달리 제시하지 않는 한, 본원에서 명쾌하게 정의되지 않은 치환기의 명명법은 부착 지점을 향하여 인접한 관능기로 이어진 관능기의 말단 부분을 좌측으로부터 우측으로 명명함으로써 도달한다. 예를 들면, 치환기 "아릴알킬옥시카르보닐"은 기 (C6-C14아릴)-(C1-C6알킬)-O-C(O)-를 지칭한다. 여기서 정의되지 않은 용어는 일반적으로 당업자에 의해 그들에 부여된 의미를 갖는다.The following definitions are used in connection with the compounds of the present invention unless the context indicates otherwise. In general, the number of carbon atoms present in a given group is designated as "C x -C y ", where x and y are the lower limit and the upper limit, respectively. For example, a group represented by "C 1 -C 6 " contains 1 to 6 carbon atoms. The carbon number as used in the definition herein refers to the carbon backbone and carbon branch, but does not include carbon atoms such as substituents such as alkoxy substitutions. Unless otherwise indicated, the nomenclature of substituents not explicitly defined herein is reached by naming the terminal portions of the functional groups leading from adjacent functional groups towards the point of attachment from left to right. For example, the substituent "arylalkyloxycarbonyl" refers to the group (C 6 -C 14 aryl)-(C 1 -C 6 alkyl) -OC (O)-. Terms not defined herein generally have the meanings assigned to them by those skilled in the art.

"아실-"은 카르보닐 관능기를 통하여 모 구조에 부착된 직쇄형, 분지형 또는 시클릭 배열 또는 그의 조합을 갖는 기를 지칭한다. 이러한 기는 포화 또는 불포화, 지방족 또는 방향족의 카르보시클릭 또는 헤테로시클릭일 수 있다. C1-C8아실-기의 예로는 아세틸-, 벤조일-, 니코티노일-, 프로피오닐-, 이소부티릴-, 옥살릴- 등이 포함된다. 저급-아실은 1개 내지 4개의 탄소를 함유하는 아실기를 지칭한다. 아실기는 비치환되거나, 또는 할로겐, H2N-, (C1-C6알킬)아미노-, 디(C1-C6알킬)아미노-, (C1-C6알킬)C(O)N(C1-C3알킬)-, (C1-C6알킬)카르복시아미도-, HC(O)NH-, H2NC(O)-, (C1-C6알킬)NHC(O)-, 디(C1-C6알킬)NC(O)-, -CN, 히드록실, C1-C6알콕시-, C1-C6알킬-, HO2C-, (C1-C6알콕시)카르보닐-, (C1-C6알킬)C(O)-, C6-C14아릴-, C1-C9헤테로아릴- 또는 C3-C8시클로알킬- 중 하나 이상으로 치환될 수 있다. "Acyl-" refers to a group having a straight, branched or cyclic arrangement or combination thereof attached to the parent structure via a carbonyl function. Such groups may be saturated or unsaturated, aliphatic or aromatic carbocyclic or heterocyclic. Examples of C 1 -C 8 acyl-groups include acetyl-, benzoyl-, nicotinoyl-, propionyl-, isobutyryl-, oxalyl- and the like. Lower-acyl refers to acyl groups containing 1 to 4 carbons. Acyl groups are unsubstituted or halogen, H 2 N-, (C 1 -C 6 alkyl) amino-, di (C 1 -C 6 alkyl) amino-, (C 1 -C 6 alkyl) C (O) N (C 1 -C 3 alkyl)-, (C 1 -C 6 alkyl) carboxamido-, HC (O) NH-, H 2 NC (O)-, (C 1 -C 6 alkyl) NHC (O) -, Di (C 1 -C 6 alkyl) NC (O)-, -CN, hydroxyl, C 1 -C 6 alkoxy-, C 1 -C 6 alkyl-, HO 2 C-, (C 1 -C 6 Alkoxy) carbonyl-, (C 1 -C 6 alkyl) C (O)-, C 6 -C 14 aryl-, C 1 -C 9 heteroaryl- or C 3 -C 8 cycloalkyl- Can be.

"알킬"은 지정된 갯수의 탄소 원자를 함유한 직쇄 또는 분지쇄일 수 있는 탄화수소 쇄를 지칭하며, 예를 들면, C1-C12알킬기는 그 안에 1 내지 12개 (포함)의 탄소 원자를 가질 수 있다. C1-C6알킬기의 예는 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 이소프로필, 이소부틸, sec-부틸, tert-부틸, 이소펜틸, 네오펜틸 및 이소헥실을 포함하지만 여기에 한정되지는 않는다. C1-C8알킬기의 예는 메틸, 프로필, 펜틸, 헥실, 헵틸, 3-메틸헥스-1-일, 2,3-디메틸펜트-2-일, 3-에틸펜트-1-일, 옥틸, 2-메틸헵트-2-일, 2,3-디메틸헥스-1-일 및 2,3,3-트리메틸펜트-1-일을 포함하지만 여기에 한정되지는 않는다. 알킬기는 비치환되거나, 또는 할로겐, -NH2, (C1-C6알킬)NH, (C1-C6알킬)(C1-C6알킬)N-, -N(C1-C3알킬)C(O)(C1-C6알킬), -NHC(O)(C1-C6알킬), -NHC(O)H, -C(O)NH2, -C(O)NH(C1-C6알킬), -C(O)N(C1-C6알킬)(C1-C6알킬), -CN, 히드록실, C1-C6알콕시, C1-C6알킬, -C(O)OH, -C(O)O(C1-C6알킬), -C(O)(C1-C6알킬), C6-C14아릴, C1-C9헤테로아릴, C3-C8시클로알킬, C1-C6할로알킬-, C1-C6아미노알킬-, -OC(O)(C1-C6알킬), C1-C6카르복시아미도알킬- 및 -NO2를 비롯한 하나 이상의 기로 치환될 수 있다. "Alkyl" refers to a hydrocarbon chain, which may be straight or branched, containing a specified number of carbon atoms, for example, a C 1 -C 12 alkyl group may have from 1 to 12 (including) carbon atoms therein. have. Examples of C 1 -C 6 alkyl groups include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl and isohexyl Does not. Examples of C 1 -C 8 alkyl groups are methyl, propyl, pentyl, hexyl, heptyl, 3-methylhex-1-yl, 2,3-dimethylpent-2-yl, 3-ethylpent-1-yl, octyl, 2-methylhept-2-yl, 2,3-dimethylhex-1-yl and 2,3,3-trimethylpent-1-yl. The alkyl group is unsubstituted or halogen, -NH 2 , (C 1 -C 6 alkyl) NH, (C 1 -C 6 alkyl) (C 1 -C 6 alkyl) N-, -N (C 1 -C 3 Alkyl) C (O) (C 1 -C 6 alkyl), -NHC (O) (C 1 -C 6 alkyl), -NHC (O) H, -C (O) NH 2 , -C (O) NH (C 1 -C 6 alkyl), -C (O) N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl), -CN, hydroxyl, C 1 -C 6 alkoxy, C 1 -C 6 Alkyl, -C (O) OH, -C (O) O (C 1 -C 6 alkyl), -C (O) (C 1 -C 6 alkyl), C 6 -C 14 aryl, C 1 -C 9 Heteroaryl, C 3 -C 8 cycloalkyl, C 1 -C 6 haloalkyl-, C 1 -C 6 aminoalkyl-, -OC (O) (C 1 -C 6 alkyl), C 1 -C 6 carboxyamide It may be substituted with one or more groups, including doalkyl- and -NO 2 .

"알카디에닐"은 2개 이상의 이중 결합을 함유하는 직쇄 또는 분지쇄 불포화 탄화수소를 지칭하고, E 또는 Z의 배열로 존재할 수 있다. C4-C6알카디에닐기의 예는 부타-1,3-디에닐, 부타-2,3-디에닐, 이소프레닐, 펜타-1,3-디에닐 및 펜타-2,4-디엔-2-일을 포함하지만 여기에 한정되지는 않는다. "Alkadienyl" refers to a straight or branched chain unsaturated hydrocarbon containing two or more double bonds and may be present in an E or Z configuration. Examples of C 4 -C 6 alkadienyl groups include buta-1,3-dienyl, buta-2,3-dienyl, isoprenyl, penta-1,3-dienyl and penta-2,4-diene- Including but not limited to 2-day.

"알카디이닐"은 2개 이상의 삼중 결합을 함유하는 직쇄 또는 분지쇄 불포화 탄화수소를 지칭한한다. C4-C6알카디이닐기의 예는 부타-1,3-디이닐, 부타-2,3-디이닐, 펜타-1,3-디이닐 및 펜타-2,4-디이닐을 포함하지만 여기에 한정되지는 않는다. "Alkadininyl" refers to a straight or branched chain unsaturated hydrocarbon containing two or more triple bonds. Examples of C 4 -C 6 alkadiinyl groups include buta-1,3-diynyl, buta-2,3-diinyl, penta-1,3-diinyl and penta-2,4-diynyl It is not limited.

"알케닐"은 1개 이상의 이중 결합을 함유하는 직쇄 또는 분지쇄 불포화 탄화수소를 지칭하고, E 또는 Z의 배열로 존재할 수 있다. C2-C8알케닐기의 예는 에틸렌, 프로필렌, 1-부틸렌, 2-부틸렌, 이소부틸렌, sec-부틸렌, 1-펜텐, 2-펜텐, 이소펜텐, 1-헥센, 2-헥센, 3-헥센, 이소헥센, 1-헵텐, 2-헵텐, 3-헵텐, 1-옥텐, 2-옥텐, 3-옥텐 및 4-옥텐을 포함하지만 여기에 한정되지는 않는다. C2-C6알케닐기의 예는 에틸렌, 프로필렌, 1-부틸렌, 2-부틸렌, 이소부틸렌, sec-부틸렌, 1-펜텐, 2-펜텐, 이소펜텐, 1-헥센, 2-헥센, 3-헥센 및 이소헥센을 포함하지만 여기에 한정되지는 않는다. C3-C8알케닐기의 예는 프로필렌, 1-부틸렌, 2-부틸렌, 이소부틸렌, sec-부틸렌, 1-펜텐, 2-펜텐, 이소펜텐, 1-헥센, 2-헥센, 3-헥센, 이소헥센, 1-헵텐, 2-헵텐, 3-헵텐, 1-옥텐, 2-옥텐, 3-옥텐 및 4-옥텐을 포함하지만 여기에 한정되지는 않는다. C3-C6알케닐기의 예는 프로프-2-에닐, 부트-3-에닐, 부트-2-에닐, 2-메티알릴, 펜트-4-에닐 및 헥스-5-에닐을 포함하지만 여기에 한정되지는 않는다. 알케닐기는 비치환되거나, 또는 할로겐, -NH2, (C1-C6알킬)NH-, (C1-C6알킬)(C1-C6알킬)N-, -N(C1-C3알킬)C(O)(C1-C6알킬), -NHC(O)(C1-C6알킬), -NHC(O)H, -C(O)NH2, -C(O)NH(C1-C6알킬), -C(O)N(C1-C6알킬)(C1-C6알킬), -CN, 히드록실, C1-C6알콕시, C1-C6알킬, -C(O)OH, -C(O)O(C1-C6알킬), -C(O)(C1-C6알킬), C6-C14아릴, C1-C9헤테로아릴 및 C3-C8시클로알킬을 비롯한 하나 이상의 기로 치환될 수 있다."Alkenyl" refers to a straight or branched chain unsaturated hydrocarbon containing one or more double bonds and may be present in an array of E or Z. Examples of C 2 -C 8 alkenyl groups are ethylene, propylene, 1-butylene, 2-butylene, isobutylene, sec-butylene, 1-pentene, 2-pentene, isopentene, 1-hexene, 2- Hexene, 3-hexene, isohexene, 1-heptene, 2-heptene, 3-heptene, 1-octene, 2-octene, 3-octene and 4-octene. Examples of C 2 -C 6 alkenyl groups are ethylene, propylene, 1-butylene, 2-butylene, isobutylene, sec-butylene, 1-pentene, 2-pentene, isopentene, 1-hexene, 2- Hexene, 3-hexene and isohexene, including but not limited to. Examples of C 3 -C 8 alkenyl groups include propylene, 1-butylene, 2-butylene, isobutylene, sec-butylene, 1-pentene, 2-pentene, isopentene, 1-hexene, 2-hexene, 3-hexene, isohexene, 1-heptene, 2-heptene, 3-heptene, 1-octene, 2-octene, 3-octene and 4-octene. Examples of C 3 -C 6 alkenyl groups include but are not limited to prop-2-enyl, but-3-enyl, but-2-enyl, 2-methallyl, pent-4-enyl and hex-5-enyl It is not limited. Alkenyl groups are unsubstituted or halogen, -NH 2 , (C 1 -C 6 alkyl) NH-, (C 1 -C 6 alkyl) (C 1 -C 6 alkyl) N-, -N (C 1- C 3 alkyl) C (O) (C 1 -C 6 alkyl), -NHC (O) (C 1 -C 6 alkyl), -NHC (O) H, -C (O) NH 2 , -C (O ) NH (C 1 -C 6 alkyl), -C (O) N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl), -CN, hydroxyl, C 1 -C 6 alkoxy, C 1- C 6 alkyl, -C (O) OH, -C (O) O (C 1 -C 6 alkyl), -C (O) (C 1 -C 6 alkyl), C 6 -C 14 aryl, C 1- It may be substituted with one or more groups including C 9 heteroaryl and C 3 -C 8 cycloalkyl.

"알키닐"은 1개 이상의 삼중 결합을 함유하는 직쇄 또는 분지쇄 불포화 탄화수소를 지칭한다. C2-C6알키닐기의 예는 아세틸렌, 프로핀, 1-부틴, 2-부틴, 이소부틴, sec-부틴, 1-펜틴, 2-펜틴, 이소펜틴, 1-헥신, 2-헥신, 3-헥신 및 이소헥신을 포함하지만 여기에 한정되지는 않는다. C3-C6알키닐기의 예는 프로프-2-이닐, 부트-3-이닐, 부트-2-이닐, 펜트-4-이닐 및 헥스-5-이닐을 포함하지만 여기에 한정되지는 않는다. C3-C8알키닐기의 예는 프로프-2-이닐, 부트-3-이닐, 부트-2-이닐, 펜트-4-이닐, 헥스-5-이닐, 헵트-3-이닐, 2-메틸헥스-3-이닐, 옥트-4-이닐 및 2-메틸헵트-3-이닐을 포함하지만 여기에 한정되지는 않는다. 알키닐기는 비치환되거나, 또는 할로겐, -NH2, (C1-C6알킬)NH, (C1-C6알킬)(C1-C6알킬)N-, -N(C1-C3알킬)C(O)(C1-C6알킬), -NHC(O)(C1-C6알킬), -NHC(O)H, -C(O)NH2, -C(O)NH(C1-C6알킬), -C(O)N(C1-C6알킬)(C1-C6알킬), -CN, 히드록실, C1-C6알콕시, C1-C6알킬, -C(O)OH, -C(O)O(C1-C6알킬), -C(O)(C1-C6알킬), C6-C14아릴, C1-C9헤테로아릴 및 C3-C8시클로알킬을 비롯한 하나 이상의 기로 치환될 수 있다. "Alkynyl" refers to a straight or branched chain unsaturated hydrocarbon containing one or more triple bonds. Examples of C 2 -C 6 alkynyl groups are acetylene, propyne, 1-butyne, 2-butyne, isobutyne, sec-butyne, 1-pentin, 2-pentin, isopentin, 1-hexine, 2-hexyne, 3 -Hexyn and isohexine, but are not limited thereto. Examples of C 3 -C 6 alkynyl groups include, but are not limited to, prop-2-ynyl, but-3-ynyl, but-2-ynyl, pent-4-ynyl and hex-5-ynyl. Examples of C 3 -C 8 alkynyl groups are prop-2-ynyl, but-3-ynyl, but-2-ynyl, pent-4-ynyl, hex-5-ynyl, hept-3-ynyl, 2-methyl Hex-3-ynyl, oct-4-ynyl and 2-methylhept-3-ynyl. Alkynyl groups are unsubstituted or halogen, -NH 2 , (C 1 -C 6 alkyl) NH, (C 1 -C 6 alkyl) (C 1 -C 6 alkyl) N-, -N (C 1 -C 3 alkyl) C (O) (C 1 -C 6 alkyl), -NHC (O) (C 1 -C 6 alkyl), -NHC (O) H, -C (O) NH 2 , -C (O) NH (C 1 -C 6 alkyl), -C (O) N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl), -CN, hydroxyl, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, -C (O) OH, -C (O) O (C 1 -C 6 alkyl), -C (O) (C 1 -C 6 alkyl), C 6 -C 14 aryl, C 1 -C 9 heteroaryl and C 3 -C 8 cycloalkyl.

"알콕시-"는 기 R-O- (여기서, R은 상기 정의한 바와 같은 알킬기임)를 지칭한다. 예시적 C1-C6알콕시-기는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, n-부톡시 및 t-부톡시를 포함하지만 여기에 한정되지 않는다. 알콕시기는 비치환되거나, 또는 할로겐, 히드록실, C1-C6알콕시-, H2N-, (C1-C6알킬)아미노-, 디(C1-C6알킬)아미노-, (C1-C6알킬)C(O)N(C1-C3알킬)-, (C1-C6알킬)카르복시아미도-, HC(O)NH-, H2NC(O)-, (C1-C6알킬)NHC(O)-, 디(C1-C6알킬)NC(O)-, NC-, C1-C6알콕시-, HO2C-, (C1-C6알콕시)카르보닐-, (C1-C6알킬)C(O)-, C6-C14아릴-, C1-C9헤테로아릴-, C3-C8시클로알킬-, C1-C6할로알킬-, 아미노(C1-C6알킬)-, (C1-C6알킬)카르복실-, C1-C6카르복시아미도알킬- 또는 O2N- 중 하나 이상의 기로 치환될 수 있다. "Alkoxy-" refers to the group RO-, wherein R is an alkyl group as defined above. Exemplary C 1 -C 6 alkoxy-groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, n-butoxy and t-butoxy. Alkoxy groups are unsubstituted or halogen, hydroxyl, C 1 -C 6 alkoxy-, H 2 N-, (C 1 -C 6 alkyl) amino-, di (C 1 -C 6 alkyl) amino-, (C 1 -C 6 alkyl) C (O) N (C 1 -C 3 alkyl)-, (C 1 -C 6 alkyl) carboxamido-, HC (O) NH-, H 2 NC (O)-, ( C 1 -C 6 alkyl) NHC (O)-, di (C 1 -C 6 alkyl) NC (O)-, NC-, C 1 -C 6 alkoxy-, HO 2 C-, (C 1 -C 6 Alkoxy) carbonyl-, (C 1 -C 6 alkyl) C (O)-, C 6 -C 14 aryl-, C 1 -C 9 heteroaryl-, C 3 -C 8 cycloalkyl-, C 1 -C 6 haloalkyl-, amino (C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl) carboxyl-, It may be substituted with one or more groups of C 1 -C 6 carboxyamidoalkyl- or O 2 N-.

"(알콕시)카르보닐-"은 기 알킬-O-C(O)-를 지칭한다. 예시적 (C1-C6알콕시)카르보닐-기는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, n-부톡시 및 t-부톡시를 포함하지만 여기에 한정되지 않는다. (알콕시)카르보닐기는 비치환되거나, 또는 할로겐, 히드록실, H2N-, (C1-C6알킬)아미노-, 디(C1-C6알킬)아미노-, (C1-C6알킬)C(O)N(C1-C3알킬)-, (C1-C6알킬)카르복시아미도-, HC(O)NH-, H2NC(O)-, (C1-C6알킬)NHC(O)-, 디(C1-C6알킬)NC(O)-, NC-, C1-C6알콕시-, HO2C-, (C1-C6알콕시)카르보닐-, (C1-C6알킬)C(O)-, C6-C14아릴-, C1-C9헤테로아릴-, C3-C8시클로알킬-, C1-C6할로알킬-, 아미노(C1-C6알킬)-, (C1-C6알킬)카르복실-, C1-C6카르복시아미도알킬- 또는 O2N- 중 하나 이상의 기로 치환될 수 있다. "(Alkoxy) carbonyl-" refers to the group alkyl-OC (O)-. Exemplary (C 1 -C 6 alkoxy) carbonyl-groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, n-butoxy and t-butoxy. The (alkoxy) carbonyl group is unsubstituted or halogen, hydroxyl, H 2 N-, (C 1 -C 6 alkyl) amino-, di (C 1 -C 6 alkyl) amino-, (C 1 -C 6 alkyl ) C (O) N (C 1 -C 3 alkyl)-, (C 1 -C 6 alkyl) carboxamido-, HC (O) NH-, H 2 NC (O)-, (C 1 -C 6 Alkyl) NHC (O)-, di (C 1 -C 6 alkyl) NC (O)-, NC-, C 1 -C 6 alkoxy-, HO 2 C-, (C 1 -C 6 alkoxy) carbonyl- , (C 1 -C 6 alkyl) C (O)-, C 6 -C 14 aryl-, C 1 -C 9 heteroaryl-, C 3 -C 8 cycloalkyl-, C 1 -C 6 haloalkyl-, amino (C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl) carboxyl-, It may be substituted with one or more groups of C 1 -C 6 carboxyamidoalkyl- or O 2 N-.

"(알킬)아미도-"는 상기 기의 질소 원자가 상기 정의한 바와 같은 C1-C6알킬기에 부착된 -C(O)NH-기를 지칭한다. (C1-C6알킬)아미도-기의 대표적인 예는 -C(O)NHCH3, -C(O)NHCH2CH3, -C(O)NHCH2CH2CH3, -C(O)NHCH2CH2CH2CH3, -C(O)NHCH2CH2CH2CH2CH3, -C(O)NHCH(CH3)2, -C(O)NHCH2CH(CH3)2, -C(O)NHCH(CH3)CH2CH3, -C(O)NH-C(CH3)3 및 -C(O)NHCH2C(CH3)3을 포함하지만 여기에 한정되지는 않는다. "(Alkyl) amido-" refers to a -C (O) NH- group wherein the nitrogen atom of said group is attached to a C 1 -C 6 alkyl group as defined above. Representative examples of (C 1 -C 6 alkyl) amido-groups are —C (O) NHCH 3 , —C (O) NHCH 2 CH 3 , —C (O) NHCH 2 CH 2 CH 3 , —C (O ) NHCH 2 CH 2 CH 2 CH 3 , -C (O) NHCH 2 CH 2 CH 2 CH 2 CH 3 , -C (O) NHCH (CH 3 ) 2 , -C (O) NHCH 2 CH (CH 3 ) 2 , -C (O) NHCH (CH 3 ) CH 2 CH 3 , -C (O) NH-C (CH 3 ) 3 and -C (O) NHCH 2 C (CH 3 ) 3 , including but not limited to It doesn't work.

"(알킬)아미노-"는 상기 기의 질소 원자가 상기 정의한 바와 같은 알킬기에 부착된 -NH기를 지칭한다. (C1-C6알킬)아미노-기의 대표적인 예는 CH3NH-, CH3CH2NH-, CH3CH2CH2NH-, CH3CH2CH2CH2NH-, (CH3)2CHNH-, (CH3)2CHCH2NH-, CH3CH2CH(CH3)NH- 및 (CH3)3CNH-를 포함하지만 여기에 한정되지 않는다. (알킬)아미노기는 비치환되거나, 또는 할로겐, H2N-, (C1-C6알킬)아미노-, 디(C1-C6알킬)아미노-, (C1-C6알킬)C(O)N(C1-C3알킬)-, (C1-C6알킬)카르복시아미도-, HC(O)NH-, H2NC(O)-, (C1-C6알킬)NHC(O)-, 디(C1-C6알킬)NC(O)-, NC-, 히드록실, C1-C6알콕시-, C1-C6알킬-, HO2C-, (C1-C6알콕시)카르보닐-, (C1-C6알킬)C(O)-, C6-C14아릴-, C1-C9헤테로아릴-, C3-C8시클로알킬-, C1-C6할로알킬-, 아미노(C1-C6알킬)-, (C1-C6알킬)카르복실-, C1-C6카르복시아미도알킬- 또는 O2N- 중 하나 이상의 기로 치환될 수 있다. "(Alkyl) amino-" refers to an -NH group wherein the nitrogen atom of said group is attached to an alkyl group as defined above. Representative examples of (C 1 -C 6 alkyl) amino-groups are CH 3 NH—, CH 3 CH 2 NH—, CH 3 CH 2 CH 2 NH—, CH 3 CH 2 CH 2 CH 2 NH—, (CH 3 ) 2 CHNH-, (CH 3 ) 2 CHCH 2 NH-, CH 3 CH 2 CH (CH 3 ) NH-, and (CH 3 ) 3 CNH-. The (alkyl) amino group is unsubstituted or halogen, H 2 N-, (C 1 -C 6 alkyl) amino-, di (C 1 -C 6 alkyl) amino-, (C 1 -C 6 alkyl) C ( O) N (C 1 -C 3 alkyl)-, (C 1 -C 6 alkyl) carboxamido-, HC (O) NH-, H 2 NC (O)-, (C 1 -C 6 alkyl) NHC (O)-, di (C 1 -C 6 alkyl) NC (O)-, NC-, hydroxyl, C 1 -C 6 alkoxy-, C 1 -C 6 alkyl-, HO 2 C-, (C 1 -C 6 alkoxy) carbonyl-, (C 1 -C 6 alkyl) C (O)-, C 6 -C 14 aryl-, C 1 -C 9 heteroaryl-, C 3 -C 8 cycloalkyl-, C 1 -C 6 haloalkyl-, amino (C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl) carboxyl-, It may be substituted with one or more groups of C 1 -C 6 carboxyamidoalkyl- or O 2 N-.

"아미노알킬-"은 알킬기의 수소 원자 중 하나 이상이 -NH2로 대체되고; NH2의 H 중 하나 또는 둘다가 치환기에 의해 대체될 수 있는, 상기 정의한 바와 같은 알킬기를 지칭한다.“Aminoalkyl-” means that at least one of the hydrogen atoms of the alkyl group is replaced with —NH 2 ; One or both H of NH 2 refers to an alkyl group as defined above, which may be replaced by a substituent.

"알킬카르복실-"은 카르복실 (C(O)-O-) 관능기의 산소 원자를 통해 모 구조에 부착된, 상기 정의한 바와 같은 알킬기를 지칭한다. (C1-C6알킬)카르복실-의 예는 아세톡시, 프로피온옥시, 프로필카르복실 및 이소펜틸카르복실을 포함한다. "Alkylcarboxyl-" refers to an alkyl group as defined above attached to the parent structure via the oxygen atom of the carboxyl (C (O) -O-) functional group. Examples of (C 1 -C 6 alkyl) carboxyl- include acetoxy, propionoxy, propylcarboxyl and isopentylcarboxyl.

"(알킬)카르복시아미도-"는 상기 기의 카르보닐 탄소 원자가 상기 정의한 바와 같은 C1-C6알킬기에 부착된 -NHC(O)-기를 지칭한다. (C1-C6알킬)카르복시아미도-기의 대표적인 예는 -NHC(O)CH3, -NHC(O)CH2CH3, -NHC(O)CH2CH2CH3, -NHC(O)CH2CH2CH2CH3, -NHC(O)CH2CH2CH2CH2CH3, -NHC(O)CH(CH3)2, -NHC(O)CH2CH(CH3)2, -NHC(O)CH(CH3)CH2CH3, -NHC(O)-C(CH3)3 및 -NHC(O)CH2C(CH3)3을 포함하지만 여기에 한정되지는 않는다. "(Alkyl) carboxamido-" refers to an -NHC (O)-group wherein the carbonyl carbon atom of said group is attached to a C 1 -C 6 alkyl group as defined above. Representative examples of (C 1 -C 6 alkyl) carboxamido-groups are —NHC (O) CH 3 , —NHC (O) CH 2 CH 3 , —NHC (O) CH 2 CH 2 CH 3 , —NHC ( O) CH 2 CH 2 CH 2 CH 3 , -NHC (O) CH 2 CH 2 CH 2 CH 2 CH 3 , -NHC (O) CH (CH 3 ) 2 , -NHC (O) CH 2 CH (CH 3 ) 2 , -NHC (O) CH (CH 3 ) CH 2 CH 3 , -NHC (O) -C (CH 3 ) 3 and -NHC (O) CH 2 C (CH 3 ) 3 , including but not limited to It doesn't work.

"알킬렌", "알케닐렌" 및 "알키닐렌"은 화학 구조내에 2개의 부착 지점을 갖는, 상기 정의한 바와 같은 알킬, 알케닐 및 알키닐기을 지칭한다. C1-C6알킬렌의 예는 에틸렌, 프로필렌 및 디메틸프로필렌을 포함한다. 마찬가지로, C2-C6알케닐렌의 예는 에테닐렌 및 프로페닐렌을 포함한다. C2-C6알키닐렌의 예는 에티닐렌 및 프로피닐렌을 포함한다. "Alkylene", "alkenylene" and "alkynylene" refer to alkyl, alkenyl and alkynyl groups as defined above having two points of attachment in the chemical structure. Examples of C 1 -C 6 alkylenes include ethylene, propylene and dimethylpropylene. Likewise, examples of C 2 -C 6 alkenylene include ethenylene and propenylene. Examples of C 2 -C 6 alkynylene include ethynylene and propynylene.

아릴은 방향족 탄화수소기를 지칭한다. C6-C14아릴기의 예는 페닐,α-나프틸, β-나프틸, 비페닐, 안트릴, 테트라히드로나프틸, 플루오레닐, 인다닐, 비페닐레닐 및 아세나나프틸을 포함하지만 여기에 한정되지는 않는다. C6-C10아릴기의 예는 페닐, α-나프틸, β-나프틸, 비페닐 및 테트라히드로나프틸을 포함하지만 여기에 한정되지는 않는다. 아릴기는 비치환되거나, 또는 C1-C6알킬, 할로, 할로알킬-, 히드록실, 히드록실(C1-C6알킬)-, -NH2, 아미노알킬-, 디알킬아미노-, -COOH, -C(O)O-(C1-C6알킬), -OC(O)(C1-C6알킬), N-알킬아미도-, -C(O)NH2, (C1-C6알킬)아미도- 또는 -NO2를 비롯한 하나 이상의 기로 치환될 수 있다.Aryl refers to an aromatic hydrocarbon group. Examples of C 6 -C 14 aryl groups include phenyl, α-naphthyl, β-naphthyl, biphenyl, anthryl, tetrahydronaphthyl, fluorenyl, indanyl, biphenylenyl and acenanaphthyl But it is not limited to this. Examples of C 6 -C 10 aryl groups include, but are not limited to, phenyl, α-naphthyl, β-naphthyl, biphenyl and tetrahydronaphthyl. The aryl group is unsubstituted or C 1 -C 6 alkyl, halo, haloalkyl-, hydroxyl, hydroxyl (C 1 -C 6 alkyl)-, -NH 2 , aminoalkyl-, dialkylamino-, -COOH , -C (O) O- (C 1 -C 6 alkyl), -OC (O) (C 1 -C 6 alkyl), N-alkylamido-, -C (O) NH 2 , (C 1- C 6 alkyl) amido- or —NO 2 may be substituted with one or more groups.

"(아릴)알킬"은 알킬기의 수소 원자 중 하나 이상을 상기 정의한 바와 같은 아릴기로 대체한, 상기 정의한 바와 같은 알킬기를 지칭한다. (C6-C14아릴)알킬- 잔기는 벤질, 벤즈히드릴, 1-페닐에틸, 2-페닐에틸, 3-페닐프로필, 2-페닐프로필, 1-나프틸메틸, 2-나프틸메틸 등을 포함한다. (아릴)알킬기는 비치환되거나, 또는 할로겐, H2N-, 히드록실, (C1-C6알킬)아미노-, 디(C1-C6알킬)아미노-, (C1-C6알킬)C(O)N(C1-C3알킬)-, (C1-C6알킬)카르복시아미도-, HC(O)NH-, H2NC(O)-, (C1-C6알킬)NHC(O)-, 디(C1-C6알킬)NC(O)-, NC-, 히드록실, C1-C6알콕시-, C1-C6알킬-, HO2C-, (C1-C6알콕시)카르보닐-, (C1-C6알킬)C(O)-, C6-C14아릴-, C1-C9헤테로아릴-, C3-C8시클로알킬-, C1-C6할로알킬-, 아미노(C1-C6알킬)-, (C1-C6알킬)카르복실-, C1-C6카르복시아미도알킬- 또는 O2N- 중 하나 이상의 기로 치환될 수 있다. "(Aryl) alkyl" refers to an alkyl group as defined above, replacing one or more of the hydrogen atoms of the alkyl group with an aryl group as defined above. (C 6 -C 14 aryl) alkyl- moieties are benzyl, benzhydryl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, 2-phenylpropyl, 1-naphthylmethyl, 2-naphthylmethyl, etc. It includes. (Aryl) alkyl group is unsubstituted or halogen, H 2 N-, hydroxyl, (C 1 -C 6 alkyl) amino-, di (C 1 -C 6 alkyl) amino-, (C 1 -C 6 alkyl ) C (O) N (C 1 -C 3 alkyl)-, (C 1 -C 6 alkyl) carboxamido-, HC (O) NH-, H 2 NC (O)-, (C 1 -C 6 Alkyl) NHC (O)-, di (C 1 -C 6 alkyl) NC (O)-, NC-, hydroxyl, C 1 -C 6 alkoxy-, C 1 -C 6 alkyl-, HO 2 C-, (C 1 -C 6 alkoxy) carbonyl-, (C 1 -C 6 alkyl) C (O)-, C 6 -C 14 aryl-, C 1 -C 9 heteroaryl-, C 3 -C 8 cycloalkyl-, C 1 -C 6 haloalkyl-, amino (C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl) carboxyl-, It may be substituted with one or more groups of C 1 -C 6 carboxyamidoalkyl- or O 2 N-.

"(아릴)아미노"는 화학식 (아릴)-NH-의 라디칼을 지칭하며, 여기서 아릴은 상기 정의한 바와 같다. "(아릴)옥시"은 기 Ar-O- (여기서, Ar는 상기 정의한 바와 같은 아릴기임)를 지칭한다. "(Aryl) amino" refers to a radical of the formula (aryl) -NH-, wherein aryl is as defined above. "(Aryl) oxy" refers to the group Ar-O-, wherein Ar is an aryl group as defined above.

"시클로알킬"은 비-방향족 포화 모노시클릭, 비시클릭 또는 폴리시클릭 탄화수소 고리계를 지칭한다. C3-C12시클로알킬의 대표적인 예는 시클로프로필, 시클로펜틸, 시클로헵틸, 시클로옥틸, 데카히드로나프탈렌-1-일, 옥타히드로-1H-인덴-2-일, 데카히드로-1H-벤조[7]안눌렌-2-일 및 도데카히드로스-인다센-4-일을 포함하지만 여기에 한정되지는 않는다. C3-C10시클로알킬의 대표적인 예는 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 시클로헵틸, 시클로옥틸, 데카히드로나프탈렌-1-일 및 옥타히드로-1H-인덴-2-일을 포함하지만 여기에 한정되지는 않는다. C3-C8시클로알킬의 대표적인 예는 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 시클로헵틸, 시클로옥틸 및 옥타히드로펜탈렌-2-일을 포함하지만 여기에 한정되지는 않는다. 시클로알킬은 비치환되거나, 또는 할로겐, -NH2, (C1-C6알킬)NH, (C1-C6알킬)(C1-C6알킬)N-, -N(C1-C3알킬)C(O)(C1-C6알킬), -NHC(O)(C1-C6알킬), -NHC(O)H, -C(O)NH2, -C(O)NH(C1-C6알킬), -C(O)N(C1-C6알킬)(C1-C6알킬), -CN, 히드록실, C1-C6알콕시, C1-C6알킬, -C(O)OH, -C(O)O(C1-C6알킬), -C(O)(C1-C6알킬), C6-C14아릴, C1-C9헤테로아릴, C3-C8시클로알킬, C1-C6할로알킬-, C1-C6아미노알킬-, -OC(O)(C1-C6알킬), C1-C6카르복시아미도알킬- 및 -NO2를 비롯한 하나 이상의 기로 치환될 수 있다. 추가로, 카르보시클릭 고리의 동일 탄소 원자 상의 임의의 2개의 수소 원자 각각은 산소 원자에 의해 대체되어 옥소 (=O) 치환기를 형성할 수 있다. "Cycloalkyl" refers to a non-aromatic saturated monocyclic, bicyclic or polycyclic hydrocarbon ring system. Representative examples of C 3 -C 12 cycloalkyl are cyclopropyl, cyclopentyl, cycloheptyl, cyclooctyl, decahydronaphthalen-1-yl, octahydro-1H-inden-2-yl, decahydro-1H-benzo [7 ] Annulen-2-yl and dodecahydros-indacene-4-yl, including but not limited to. Representative examples of C 3 -C 10 cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, decahydronaphthalen-1-yl and octahydro-1H-inden-2-yl It is not limited to this. Representative examples of C 3 -C 8 cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and octahydropentalen-2-yl. Cycloalkyl is unsubstituted or halogen, -NH 2 , (C 1 -C 6 alkyl) NH, (C 1 -C 6 alkyl) (C 1 -C 6 alkyl) N-, -N (C 1 -C 3 alkyl) C (O) (C 1 -C 6 alkyl), -NHC (O) (C 1 -C 6 alkyl), -NHC (O) H, -C (O) NH 2 , -C (O) NH (C 1 -C 6 alkyl), -C (O) N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl), -CN, hydroxyl, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, -C (O) OH, -C (O) O (C 1 -C 6 alkyl), -C (O) (C 1 -C 6 alkyl), C 6 -C 14 aryl, C 1 -C 9 heteroaryl, C 3 -C 8 cycloalkyl, C 1 -C 6 haloalkyl-, C 1 -C 6 aminoalkyl-, -OC (O) (C 1 -C 6 alkyl), C 1 -C 6 carboxy It may be substituted with one or more groups, including amidoalkyl- and -NO 2 . In addition, each of any two hydrogen atoms on the same carbon atom of the carbocyclic ring may be replaced by an oxygen atom to form an oxo (═O) substituent.

"시클로알케닐"은 2개의 고리 탄소 원자를 연결시키는 1개 이상의 이중 결합을 함유하는, 비-방향족 불포화 모노시클릭, 비시클릭 또는 폴리시클릭 탄화수소 고리계를 지칭한다. C5-C8시클로알케닐의 대표적인 예는 시클로펜테닐, 시클로헥세닐, 4,4a-옥탈린-3-일 및 시클로옥테닐을 포함하지만 여기에 한정되지는 않는다. 시클로알케닐은 비치환되거나, 또는 할로겐, -NH2, (C1-C6알킬)NH, (C1-C6알킬)(C1-C6알킬)N-, -N(C1-C3알킬)C(O)(C1-C6알킬), -NHC(O)(C1-C6알킬), -NHC(O)H, -C(O)NH2, -C(O)NH(C1-C6알킬), -C(O)N(C1-C6알킬)(C1-C6알킬), -CN, 히드록실, C1-C6알콕시, C1-C6알킬, -C(O)OH, -C(O)O(C1-C6알킬), -C(O)(C1-C6알킬), C6-C14아릴, C1-C9헤테로아릴 및 C3-C8시클로알킬을 비롯한 하나 이상의 기로 치환될 수 있다. 추가로, 카르보시클릭 고리의 동일 탄소 원자 상의 임의의 2개의 수소 원자 각각은 산소 원자에 의해 대체되어 옥소 (=O) 치환기를 형성할 수 있다. "Cycloalkenyl" refers to a non-aromatic unsaturated monocyclic, bicyclic, or polycyclic hydrocarbon ring system containing one or more double bonds connecting two ring carbon atoms. Representative examples of C 5 -C 8 cycloalkenyl include, but are not limited to, cyclopentenyl, cyclohexenyl, 4,4a-octalin-3-yl and cyclooctenyl. Cycloalkenyl is unsubstituted or halogen, -NH 2 , (C 1 -C 6 alkyl) NH, (C 1 -C 6 alkyl) (C 1 -C 6 alkyl) N-, -N (C 1- C 3 alkyl) C (O) (C 1 -C 6 alkyl), -NHC (O) (C 1 -C 6 alkyl), -NHC (O) H, -C (O) NH 2 , -C (O ) NH (C 1 -C 6 alkyl), -C (O) N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl), -CN, hydroxyl, C 1 -C 6 alkoxy, C 1- C 6 alkyl, -C (O) OH, -C (O) O (C 1 -C 6 alkyl), -C (O) (C 1 -C 6 alkyl), C 6 -C 14 aryl, C 1- It may be substituted with one or more groups including C 9 heteroaryl and C 3 -C 8 cycloalkyl. In addition, each of any two hydrogen atoms on the same carbon atom of the carbocyclic ring may be replaced by an oxygen atom to form an oxo (═O) substituent.

"디(알킬)아미노-"는 상기 정의한 바와 같은 2개의 알킬기에 부착된 질소 원자를 지칭한다. 각각 알킬기는 독립적으로 선택될 수 있다. 디(C1-C6알킬)아미노-기의 대표적인 예는 -N(CH3)2, -N(CH2CH3)(CH3), -N(CH2CH3)2, -N(CH2CH2CH3)2, -N(CH2CH2CH2CH3)2, -N(CH(CH3)2)2, -N(CH(CH3)2)(CH3), -N(CH2CH(CH3)2)2, -NH(CH(CH3)CH2CH3)2, -N(C(CH3)3)2, -N(C(CH3)3)(CH3) 및 -N(CH3)(CH2CH3)을 포함하지만 여기에 한정되지는 않는다. 질소 원자 상의 2개의 알킬기는, 이들이 부착되어 있는 질소와 함께, 3원 내지 7원의, 질소 함유 헤테로사이클을 형성할 수 있고, 여기서 상기 헤테로사이클의 탄소 원자 중 2개 이상은 -N(H)-, -N(C1-C6알킬)-, -N(C3-C8시클로알킬)-, -N(C6-C14아릴)-, -N(C1-C9헤테로아릴)-, -N(아미노(C1-C6알킬))-, -N(C6-C14아릴아미노)-, -O-, -S-, -S(O)- 또는 -S(O)2-로 대체될 수 있다. "Di (alkyl) amino-" refers to a nitrogen atom attached to two alkyl groups as defined above. Each alkyl group can be selected independently. Representative examples of di (C 1 -C 6 alkyl) amino-groups include —N (CH 3 ) 2 , —N (CH 2 CH 3 ) (CH 3 ), —N (CH 2 CH 3 ) 2 , —N ( CH 2 CH 2 CH 3 ) 2 , -N (CH 2 CH 2 CH 2 CH 3 ) 2 , -N (CH (CH 3 ) 2 ) 2 , -N (CH (CH 3 ) 2 ) (CH 3 ), -N (CH 2 CH (CH 3 ) 2 ) 2 , -NH (CH (CH 3 ) CH 2 CH 3 ) 2 , -N (C (CH 3 ) 3 ) 2, -N (C (CH 3 ) 3 ) (CH 3 ) and -N (CH 3 ) (CH 2 CH 3 ). Two alkyl groups on a nitrogen atom may, together with the nitrogen to which they are attached, form a three to seven membered nitrogen-containing heterocycle, wherein at least two of the carbon atoms of the heterocycle are -N (H) -, -N (C 1 -C 6 alkyl)-, -N (C 3 -C 8 cycloalkyl)-, -N (C 6 -C 14 aryl)-, -N (C 1 -C 9 heteroaryl) -, -N (amino (C 1 -C 6 alkyl))-, -N (C 6 -C 14 arylamino)-, -O-, -S-, -S (O)-or -S (O) Can be replaced with 2- .

"할로" 또는 "할로겐"은 -F, -Cl, -Br 및 -I를 지칭한다."Halo" or "halogen" refers to -F, -Cl, -Br and -I.

"C1-C6할로알킬-"은 C1-C6알킬기의 수소 원자 중 하나 이상이 -F, -Cl, -Br 또는 -I로 대체된, 상기 정의한 바와 같은 C1-C6알킬기를 지칭한다. 각각의 치환은 -F, -Cl, -Br 또는 -I로부터 독립적으로 선택될 수 있다. C1-C6할로알킬-기의 대표적인 예는 -CH2F, -CCl3, -CF3, CH2CF3, -CH2Cl, -CH2CH2Br, -CH2CH2I, -CH2CH2CH2F, -CH2CH2CH2Cl, -CH2CH2CH2CH2Br, -CH2CH2CH2CH2I, -CH2CH2CH2CH2CH2Br, -CH2CH2CH2CH2CH2I, -CH2CH(Br)CH3, -CH2CH(Cl)CH2CH3, -CH(F)CH2CH3 및 -C(CH3)2(CH2Cl)을 포함하지만 여기에 한정되지는 않는다. "C 1 -C 6 haloalkyl" is one or more of the hydrogen atoms of the C 1 -C 6 alkyl group is replaced by -F, -Cl, -Br or -I, a C 1 -C 6 alkyl group as defined above, Refer. Each substitution may be independently selected from -F, -Cl, -Br or -I. Representative examples of C 1 -C 6 haloalkyl-groups are —CH 2 F, —CCl 3 , —CF 3 , CH 2 CF 3 , —CH 2 Cl, —CH 2 CH 2 Br, —CH 2 CH 2 I, -CH 2 CH 2 CH 2 F, -CH 2 CH 2 CH 2 Cl, -CH 2 CH 2 CH 2 CH 2 Br, -CH 2 CH 2 CH 2 CH 2 I, -CH 2 CH 2 CH 2 CH 2 CH 2 Br, -CH 2 CH 2 CH 2 CH 2 CH 2 I, -CH 2 CH (Br) CH 3 , -CH 2 CH (Cl) CH 2 CH 3 , -CH (F) CH 2 CH 3 and -C (CH 3 ) 2 (CH 2 Cl), but not limited thereto.

"헤테로아릴"은 헤테로원자 산소, 황 및 질소로부터 선택된 하나 이상의 고리 원자를 함유하는 모노시클릭, 비시클릭 또는 폴리시클릭 방향족 고리계를 지칭한다. C1-C9헤테로아릴기의 예는 푸란, 티오펜, 인돌, 아자인돌, 옥사졸, 티아졸, 이속사졸, 이소티아졸, 이미다졸, N-메틸이미다졸, 피리딘, 피리미딘, 피라진, 피롤, N-메틸피롤, 피라졸, N-메틸피라졸, 1,3,4-옥사디아졸, 1,2,4-트리아졸, 1-메틸-1,2,4-트리아졸, 1H-테트라졸, 1-메틸테트라졸, 벤즈옥사졸, 벤조티아졸, 벤조푸란, 벤즈이속사졸, 벤즈이미다졸, N-메틸벤즈이미다졸, 아자벤즈이미다졸, 인다졸, 퀴나졸린, 퀴놀린 및 이소퀴놀린을 포함한다. 비시클릭 C1-C9헤테로아릴기는 페닐, 피리딘, 피리미딘 또는 피리다진 고리가 고리 내에 1 또는 2개의 질소 원자 (1개의 질소 원자는 고리 내의 1개의 산소 또는 1개의 황 원자와 함께임) 또는 1개의 O 또는 S 고리 원자를 갖는 5원 또는 6원 모노시클릭 헤테로아릴 고리에 융합되는 것들이다. 모노시클릭 C1-C4헤테로아릴기의 예는 2H-테트라졸, 3H-1,2,4-트리아졸, 푸란, 티오펜, 옥사졸, 티아졸, 이속사졸, 이소티아졸, 이미다졸 및 피롤을 포함한다. 헤테로아릴기는 비치환되거나, 또는 C1-C6알킬, 할로, 할로알킬-, 히드록실, 히드록실(C1-C6알킬)-, -NH2, 아미노알킬-, 디알킬아미노-, -COOH, -C(O)O-(C1-C6알킬), -OC(O)(C1-C6알킬), N-알킬아미도-, -C(O)NH2, (C1-C6알킬)아미도- 또는 -NO2를 비롯한 하나 이상의 기로 치환될 수 있다. "Heteroaryl" refers to a monocyclic, bicyclic or polycyclic aromatic ring system containing one or more ring atoms selected from heteroatoms oxygen, sulfur and nitrogen. Examples of C 1 -C 9 heteroaryl groups include furan, thiophene, indole, azaindole, oxazole, thiazole, isoxazole, isothiazole, imidazole, N-methylimidazole, pyridine, pyrimidine, pyrazine , Pyrrole, N-methylpyrrole, pyrazole, N-methylpyrazole, 1,3,4-oxadiazole, 1,2,4-triazole, 1-methyl-1,2,4-triazole, 1H Tetrazole, 1-methyltetrazole, benzoxazole, benzothiazole, benzofuran, benzisoxazole, benzimidazole, N-methylbenzimidazole, azabenzimidazole, indazole, quinazoline, quinoline and iso Contains quinoline. A bicyclic C 1 -C 9 heteroaryl group is a phenyl, pyridine, pyrimidine or pyridazine ring in which one or two nitrogen atoms in the ring (one nitrogen atom is with one oxygen or one sulfur atom in the ring) or And fused to 5- or 6-membered monocyclic heteroaryl rings having one O or S ring atom. Examples of monocyclic C 1 -C 4 heteroaryl groups include 2H-tetrazole, 3H-1,2,4-triazole, furan, thiophene, oxazole, thiazole, isoxazole, isothiazole, imidazole And pyrrole. Heteroaryl groups are unsubstituted or C 1 -C 6 alkyl, halo, haloalkyl-, hydroxyl, hydroxyl (C 1 -C 6 alkyl)-, -NH 2 , aminoalkyl-, dialkylamino-,- COOH, -C (O) O- ( C 1 -C 6 alkyl), -OC (O) (C 1 -C 6 alkyl), N- alkyl amido -, -C (O) NH 2 , (C 1 -C 6 alkyl) amido- or -NO 2 may be substituted with one or more groups.

"(헤테로아릴)알킬-"은 알킬기의 수소 원자 중 하나 이상을 상기 정의한 바와 같은 헤테로아릴로 대체한, 상기 정의한 바와 같은 알킬기를 지칭한다. (C1-C9헤테로아릴)알킬- 잔기의 예는 2-피리딜메틸, 2-티오페닐에틸, 3-피리딜프로필, 2-퀴놀리닐메틸, 2-인돌릴메틸 등을 포함한다. (헤테로아릴)알킬기는 비치환되거나, 또는 할로겐, H2N-, 히드록실, (C1-C6알킬)아미노-, 디(C1-C6알킬)아미노-, (C1-C6알킬)C(O)N(C1-C3알킬)-, (C1-C6알킬)카르복시아미도-, HC(O)NH-, H2NC(O)-, (C1-C6알킬)NHC(O)-, 디(C1-C6알킬)NC(O)-, NC-, 히드록실, C1-C6알콕시-, C1-C6알킬-, HO2C-, (C1-C6알콕시)카르보닐-, (C1-C6알킬)C(O)-, C6-C14아릴-, C1-C9헤테로아릴-, C3-C8시클로알킬-, C1-C6할로알킬-, 아미노(C1-C6알킬)-, (C1-C6알킬)카르복실-, C1-C6카르복시아미도알킬- 또는 O2N- 중 하나 이상의 기로 치환될 수 있다. "(Heteroaryl) alkyl-" refers to an alkyl group as defined above, wherein at least one of the hydrogen atoms of the alkyl group is replaced by heteroaryl as defined above. Examples of (C 1 -C 9 heteroaryl) alkyl- moieties include 2-pyridylmethyl, 2-thiophenylethyl, 3-pyridylpropyl, 2-quinolinylmethyl, 2-indolylmethyl, and the like. The (heteroaryl) alkyl group is unsubstituted or halogen, H 2 N-, hydroxyl, (C 1 -C 6 alkyl) amino-, di (C 1 -C 6 alkyl) amino-, (C 1 -C 6 Alkyl) C (O) N (C 1 -C 3 alkyl)-, (C 1 -C 6 alkyl) carboxamido-, HC (O) NH-, H 2 NC (O)-, (C 1 -C 6 alkyl) NHC (O)-, di (C 1 -C 6 alkyl) NC (O)-, NC-, hydroxyl, C 1 -C 6 alkoxy-, C 1 -C 6 alkyl-, HO 2 C- , (C 1 -C 6 alkoxy) carbonyl-, (C 1 -C 6 alkyl) C (O)-, C 6 -C 14 aryl-, C 1 -C 9 heteroaryl-, C 3 -C 8 cycloalkyl-, C 1 -C 6 haloalkyl-, amino (C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl) carboxyl-, It may be substituted with one or more groups of C 1 -C 6 carboxyamidoalkyl- or O 2 N-.

용어 "헤테로원자"는 황, 질소 또는 산소 원자를 지칭한다. The term "heteroatom" refers to a sulfur, nitrogen or oxygen atom.

"헤테로사이클" 또는 "헤테로시클릴"은 1개 이상의 고리 원자가 헤테로원자인 모노시클릭, 비시클릭 및 폴리시클릭기를 지칭한다. 헤테로사이클은 포화 또는 부분 포화일 수 있다. 예시적 C1-C9헤테로시클릴-기는 아지리딘, 옥시란, 옥시렌, 티이란, 피롤린, 피롤리딘, 디히드로푸란, 테트라히드로푸란, 디히드로티오펜, 테트라히드로티오펜, 디티올란, 피페리딘, 1,2,3,6-테트라히드로피리딘-1-일, 테트라히드로피란, 피란, 티안, 티인, 피페라진, 옥사진, 5,6-디히드로-4H-1,3-옥사진-2-일, 2,5-디아자비시클로[2.2.1]헵탄, 2,5-디아자비시클로[2.2.2]옥탄, 3,6-디아자비시클로[3.1.1]헵탄, 3,8-디아자비시클로[3.2.1]옥탄, 6-옥사-3,8-디아자비시클로[3.2.1]옥탄, 7-옥사-2,5-디아자비시클로[2.2.2]옥탄, 2,7-디옥사-5-아자비시클로[2.2.2]옥탄, 2-옥사-5-아자비시클로[2.2.1]헵탄-5-일, 2-옥사-5-아자비시클로[2.2.2]옥탄, 3,6-디옥사-8-아자비시클로[3.2.1]옥탄, 3-옥사-6-아자비시클로[3.1.1]헵탄, 3-옥사-8-아자비시클로[3.2.1]옥탄-8-일, 5,7-디옥사-2-아자비시클로[2.2.2]옥탄, 6,8-디옥사-3-아자비시클로[3.2.1]옥탄, 6-옥사-3-아자비시클로[3.1.1]헵탄, 8-옥사-3-아자비시클로[3.2.1]옥탄-3-일, 2-메틸-2,5-디아자비시클로[2.2.1]헵탄-5-일, 1,3,3-트리메틸-6-아자비시클로[3.2.1]옥트-6-일, 3-히드록시-8-아자비시클로[3.2.1]옥탄-8-일-, 7-메틸-3-옥사-7,9-디아자비시클로[3.3.1]노난-9-일, 9-옥사-3-아자비시클로[3.3.1]노난-3-일, 3-옥사-9-아자비시클로[3.3.1]노난-9-일, 3,7-디옥사-9-아자비시클로[3.3.1]노난-9-일, 4-메틸-3,4-디히드로-2H-1,4-벤즈옥사진-7-일, 티아진, 디티안 및 디옥산을 포함하지만 여기에 한정되지는 않는다. 구체적 헤테로사이클 고리 또는 고리계는 최소 3원을 갖는다. 따라서, 예를 들면, C1헤테로시클릴- 라디칼은 옥사지라닐, 디아지리디닐 및 디아지리닐을 포함하지만 여기에 한정되지 않고, C2헤테로시클릴- 라디칼은 아지리디닐, 옥시라닐 및 디아제티디닐을 포함하지만 여기에 한정되지 않고, C9헤테로시클릴- 라디칼은 아제카닐, 테트라히드로퀴놀리닐 및 퍼이드로이소퀴놀리닐을 포함하지만 여기에 한정되지 않는다. 헤테로시클릴기는 비치환되거나, 또는 C1-C6알킬, 할로, 할로알킬-, 히드록실, 히드록실(C1-C6알킬)-, -NH2, 아미노알킬-, 디알킬아미노-, -COOH, -C(O)O-(C1-C6알킬), -OC(O)(C1-C6알킬), N-알킬아미도-, -C(O)NH2, (C1-C6알킬)아미도- 또는 -NO2를 비롯한 하나 이상의 기로 치환될 수 있다."Heterocycle" or "heterocyclyl" refers to monocyclic, bicyclic and polycyclic groups in which one or more ring atoms is a heteroatom. Heterocycles may be saturated or partially saturated. Exemplary C 1 -C 9 heterocyclyl-groups are aziridine, oxirane, oxylene, tyran, pyrroline, pyrrolidine, dihydrofuran, tetrahydrofuran, dihydrothiophene, tetrahydrothiophene, dithiyl Olan, piperidine, 1,2,3,6-tetrahydropyridin-1-yl, tetrahydropyran, pyran, thian, thyine, piperazine, oxazine, 5,6-dihydro-4H-1,3 Oxazin-2-yl, 2,5-diazabicyclo [2.2.1] heptane, 2,5-diazabicyclo [2.2.2] octane, 3,6-diazabicyclo [3.1.1] heptane, 3,8-diazabicyclo [3.2.1] octane, 6-oxa-3,8-diazabicyclo [3.2.1] octane, 7-oxa-2,5-diazabicyclo [2.2.2] octane, 2,7-dioxa-5-azabicyclo [2.2.2] octane, 2-oxa-5-azabicyclo [2.2.1] heptan-5-yl, 2-oxa-5-azabicyclo [2.2.2] Octane, 3,6-dioxa-8-azabicyclo [3.2.1] octane, 3-oxa-6-azabicyclo [3.1.1] heptane, 3-oxa-8-azabicyclo [3.2.1] octane- 8-yl, 5,7-dioxa-2-azabicyclo [2.2.2] octane, 6,8- Oxa-3-azabicyclo [3.2.1] octane, 6-oxa-3-azabicyclo [3.1.1] heptane, 8-oxa-3-azabicyclo [3.2.1] octan-3-yl, 2-methyl -2,5-diazabicyclo [2.2.1] heptan-5-yl, 1,3,3-trimethyl-6-azabicyclo [3.2.1] oct-6-yl, 3-hydroxy-8-azabi Cyclo [3.2.1] octane-8-yl-, 7-methyl-3-oxa-7,9-diazabicyclo [3.3.1] nonan-9-yl, 9-oxa-3-azabicyclo [3.3. 1] nonan-3-yl, 3-oxa-9-azabicyclo [3.3.1] nonan-9-yl, 3,7-dioxa-9-azabicyclo [3.3.1] nonan-9-yl, 4 -Methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl, thiazine, dithiane and dioxane. Specific heterocycle rings or ring systems have at least three members. Thus, for example, C 1 heterocyclyl- radicals include, but are not limited to, oxaziriranyl, diaziridinyl and diazirinyl, and C 2 heterocyclyl- radicals include aziridinyl, oxiranyl and diadia Including but not limited to zetidinyl, C 9 heterocyclyl-radicals include, but are not limited to, azecanyl, tetrahydroquinolinyl and perfluoroisoquinolinyl. Heterocyclyl groups are unsubstituted or C 1 -C 6 alkyl, halo, haloalkyl-, hydroxyl, hydroxyl (C 1 -C 6 alkyl)-, -NH 2 , aminoalkyl-, dialkylamino-, -COOH, -C (O) O- ( C 1 -C 6 alkyl), -OC (O) (C 1 -C 6 alkyl), N- alkyl amido -, -C (O) NH 2 , (C It may be substituted with one or more groups, including 1 -C 6 alkyl) amido- or -NO 2 .

"헤테로시클릴(알킬)-"은 알킬기의 수소 원자 중 1개 이상이 상기 정의한 바와 같은 헤테로사이클기로 대체된, 상기 정의한 바와 같은 알킬기를 지칭한다. 헤테로시클릴(C1-C6알킬)- 잔기는 2-피리딜메틸, 1-피페라지닐에틸, 4-모르폴리닐프로필, 6-피페라지닐헥실 등을 포함한다. 헤테로시클릴(알킬)기는 비치환되거나, 또는 할로겐, H2N-, (C1-C6알킬)아미노-, 디(C1-C6알킬)아미노-, (C1-C6알킬)C(O)N(C1-C3알킬)-, (C1-C6알킬)카르복시아미도-, HC(O)NH-, H2NC(O)-, (C1-C6알킬)NHC(O)-, 디(C1-C6알킬)NC(O)-, NC-, 히드록실, C1-C6알콕시-, C1-C6알킬-, HO2C-, (C1-C6알콕시)카르보닐-, (C1-C6알킬)C(O)-, 4 내지 7원 모노시클릭 헤테로사이클, C6-C14아릴-, C1-C9헤테로아릴- 또는 C3-C8시클로알킬- 중 하나 이상의 기로 치환될 수 있다. "Heterocyclyl (alkyl)-" refers to an alkyl group as defined above, wherein at least one of the hydrogen atoms of the alkyl group is replaced with a heterocycle group as defined above. Heterocyclyl (C 1 -C 6 alkyl)-moieties include 2-pyridylmethyl, 1-piperazinylethyl, 4-morpholinylpropyl, 6-piperazinylhexyl, and the like. Heterocyclyl (alkyl) groups are unsubstituted or halogen, H 2 N-, (C 1 -C 6 alkyl) amino-, di (C 1 -C 6 alkyl) amino-, (C 1 -C 6 alkyl) C (O) N (C 1 -C 3 alkyl)-, (C 1 -C 6 alkyl) carboxamido-, HC (O) NH-, H 2 NC (O)-, (C 1 -C 6 alkyl ) NHC (O)-, di (C 1 -C 6 alkyl) NC (O)-, NC-, hydroxyl, C 1 -C 6 alkoxy-, C 1 -C 6 alkyl-, HO 2 C-, ( C 1 -C 6 alkoxy) carbonyl-, (C 1 -C 6 alkyl) C (O)-, 4-7 membered monocyclic heterocycle, C 6 -C 14 aryl-, It may be substituted with one or more groups of C 1 -C 9 heteroaryl- or C 3 -C 8 cycloalkyl-.

"히드록시알킬-"은 알킬기의 수소 원자 중 1개 이상이 히드록실기로 대체된, 상기 정의한 바와 같은 알킬기를 지칭한다. C1-C6히드록시알킬- 잔기의 예는, 예를 들어, -CH2OH, -CH2CH2OH, -CH2CH2CH2OH, -CH2CH(OH)CH2OH, -CH2CH(OH)CH3, -CH(CH3)CH2OH 및 고도의 동족체를 포함한다. "Hydroxyalkyl-" refers to an alkyl group as defined above, wherein at least one of the hydrogen atoms of the alkyl group is replaced with a hydroxyl group. Examples of C 1 -C 6 hydroxyalkyl- moieties are, for example, —CH 2 OH, —CH 2 CH 2 OH, —CH 2 CH 2 CH 2 OH, —CH 2 CH (OH) CH 2 OH, -CH 2 CH (OH) CH 3 , -CH (CH 3 ) CH 2 OH, and highly homologs.

"모노시클릭 헤테로시클릴"은 1개 이상의 고리 원자가 헤테로원자인 모노시클릭기를 지칭한다. 헤테로사이클은 포화 또는 부분 포화일 수 있다. 예시적 모노시클릭 C1-C9헤테로시클릴-기는 아지리딘, 옥시란, 옥시렌, 티이란, 피롤린, 피롤리딘, 디히드로푸란, 테트라히드로푸란, 디히드로티오펜, 테트라히드로티오펜, 디티올란, 피페리딘, 1,2,3,6-테트라히드로피리딘-1-일, 테트라히드로피란, 피란, 티안, 티인, 피페라진, 옥사진, 5,6-디히드로-4H-1,3-옥사진-2-일, 4-메틸-3,4-디히드로-2H-1,4-벤즈옥사진-7-일, 티아진, 디티안 및 디옥산을 포함하지만 여기에 한정되지 않는다. 구체적 헤테로사이클 고리계는 최소 3원을 갖는다. 따라서, 예를 들면, C1헤테로시클릴- 라디칼은 옥사지라닐, 디아지리디닐 및 디아지리닐을 포함하지만 여기에 한정되지 않고, C2헤테로시클릴- 라디칼은 아지리디닐, 옥시라닐 및 디아제티디닐을 포함하지만 여기에 한정되지 않고, C9헤테로시클릴- 라디칼은 아제카닐을 포함하지만 여기에 한정되지 않는다. 헤테로시클릴기는 비치환되거나, 또는 C1-C6알킬, 할로, 할로알킬-, 히드록실, 히드록실(C1-C6알킬)-, -NH2, 아미노알킬-, 디알킬아미노-, -COOH, -C(O)O-(C1-C6알킬), -OC(O)(C1-C6알킬), N-알킬아미도-, -C(O)NH2, (C1-C6알킬)아미도- 또는 -NO2를 비롯한 하나 이상의 기로 치환될 수 있다."Monocyclic heterocyclyl" refers to a monocyclic group wherein at least one ring atom is a heteroatom. Heterocycles may be saturated or partially saturated. Exemplary monocyclic C 1 -C 9 heterocyclyl-groups are aziridine, oxirane, oxylene, tyran, pyrroline, pyrrolidine, dihydrofuran, tetrahydrofuran, dihydrothiophene, tetrahydroti Offen, dithiolane, piperidine, 1,2,3,6-tetrahydropyridin-1-yl, tetrahydropyran, pyran, thian, thyine, piperazine, oxazine, 5,6-dihydro-4H- 1,3-oxazin-2-yl, 4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl, thiazine, dithiane and dioxane It doesn't work. Specific heterocycle ring systems have at least three members. Thus, for example, C 1 heterocyclyl- radicals include, but are not limited to, oxaziriranyl, diaziridinyl and diazirinyl, and C 2 heterocyclyl- radicals include aziridinyl, oxiranyl and diadia Including but not limited to zetidinyl, C 9 heterocyclyl- radicals include but are not limited to azecanyl. Heterocyclyl groups are unsubstituted or C 1 -C 6 alkyl, halo, haloalkyl-, hydroxyl, hydroxyl (C 1 -C 6 alkyl)-, -NH 2 , aminoalkyl-, dialkylamino-, -COOH, -C (O) O- ( C 1 -C 6 alkyl), -OC (O) (C 1 -C 6 alkyl), N- alkyl amido -, -C (O) NH 2 , (C It may be substituted with one or more groups, including 1 -C 6 alkyl) amido- or -NO 2 .

"퍼플루오로알킬-"은 2개 이상의 불소 원자 갖는, 상기에 정의한 알킬기를 지칭한다. C1-C6퍼플루오로알킬-기의 예는 CF3, CH2CF3, CF2CF3 및 CH(CF3)2를 포함한다. "Perfluoroalkyl-" refers to an alkyl group as defined above having two or more fluorine atoms. Examples of C 1 -C 6 perfluoroalkyl-groups include CF 3 , CH 2 CF 3 , CF 2 CF 3 and CH (CF 3 ) 2 .

"대상체"는 포유동물, 예를 들어, 인간, 마우스, 래트, 기니아 피그, 개, 고양이, 말, 소, 돼지 또는 비-인간 영장류, 예컨대 원숭이, 침팬지, 개코원숭이 또는 고릴라이다. A “subject” is a mammal, eg, a human, mouse, rat, guinea pig, dog, cat, horse, cow, pig, or non-human primate such as monkey, chimpanzee, baboon or gorilla.

본원에 사용된 바와 같은 용어 "임의로 치환된"은 1개 이상의 수소 원자가 할로겐, -NH2, -NH(C1-C6알킬), -N(C1-C6알킬)(C1-C6알킬), -N(C1-C3알킬)C(O)(C1-C6알킬), -NHC(O)(C1-C6알킬), -NHC(O)H, -C(O)NH2, -C(O)NH(C1-C6알킬), -C(O)N(C1-C6알킬)(C1-C6알킬), -CN, 히드록실, C1-C6알콕시, C1-C6알킬, -C(O)OH, -C(O)O(C1-C6알킬), -C(O)(C1-C6알킬), C6-C14아릴, C1-C9헤테로아릴 또는 C3-C8시클로알킬로 치환된 것을 의미한다.As used herein, the term "optionally substituted" means that at least one hydrogen atom is halogen, -NH 2 , -NH (C 1 -C 6 alkyl), -N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl), -N (C 1 -C 3 alkyl) C (O) (C 1 -C 6 alkyl), -NHC (O) (C 1 -C 6 alkyl), -NHC (O) H, -C (O) NH 2 , -C (O) NH (C 1 -C 6 alkyl), -C (O) N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl), -CN, hydroxyl, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, -C (O) OH, -C (O) O (C 1 -C 6 alkyl), -C (O) (C 1 -C 6 alkyl), C 6 -C 14 aryl , C 1 -C 9 heteroaryl or C 3 -C 8 cycloalkyl.

대표하는 "제약상 허용되는 염"은, 예를 들어 수용성 및 수불용성 염, 예컨대 아세테이트, 알루미늄, 암소네이트 (4,4-디아미노스틸벤-2,2-디술포네이트), 벤자틴 (N,N'-디벤질에틸렌디아민), 벤젠술포네이트, 벤조에이트, 비카르보네이트, 비스무트, 비술페이트, 비타르트레이트, 보레이트, 브로마이드, 부티레이트, 칼슘, 칼슘 에데테이트, 캄실레이트 (캄포르술포네이트), 카르보네이트, 클로라이드, 콜린, 시트레이트, 클라불라리에이트, 디에탄올아민, 디히드로클로라이드, 디포스페이트, 에데테이트, 에디실레이트 (캄포르술포네이트), 에실레이트 (에탄술포네이트), 에틸렌디아민, 푸마레이트, 글루셉테이트 (글루코헵토네이트), 글루코네이트, 글루쿠로네이트, 글루타메이트, 헥사플루오로포스페이트, 헥실레소르시네이트, 히드라바민 (N,N'-비스(데히드로아비에틸)에틸렌디아민), 히드로브로마이드, 히드로클로라이드, 히드록시나프토에이트, 1-히드록시-2-나프토에이트, 3-히드록시-2-나프토에이트, 요오다이드, 이소티오네이트 (2-히드록시에탄술포네이트), 락테이트, 락토비오네이트, 라우레이트, 라우릴 술페이트, 리튬, 마그네슘, 말레이트, 말레에이트, 만델레이트, 메글루민 (1-데옥시-1-(메틸아미노)-D-글루시톨), 메실레이트, 메틸 브로마이드, 메틸니트레이트, 메틸술페이트, 뮤케이트, 납실레이트, 니트레이트, N-메틸글루카민 암모늄 염, 올레에이트, 옥살레이트, 팔미테이트, 파모에이트 (4,4'-메틸렌비스-3-히드록시-2-나프토에이트 또는 엠보네이트), 판토테네이트, 포스페이트, 피크레이트, 폴리갈락투로네이트, 칼륨, 프로피오네이트, p-톨루엔술포네이트, 살리실레이트, 나트륨, 스테아레이트, 서브아세테이트, 숙시네이트, 술페이트, 술포살리쿨레이트, 수라메이트, 탄네이트, 타르트레이트, 테오클레이트 (8-클로로-3,7-디히드로-1,3-디메틸-1H-퓨린-2,6-디온), 트리에티오다이드, 트로메타민 (2-아미노-2-(히드록시메틸)-1,3-프로판디올), 발레레이트 및 아연 염을 포함하나 여기에 한정되지 않는다. Representative "pharmaceutically acceptable salts" include, for example, water soluble and water insoluble salts such as acetates, aluminum, hemateate (4,4-diaminostilben-2,2-disulfonate), benzine (N , N'-dibenzylethylenediamine), benzenesulfonate, benzoate, bicarbonate, bismuth, bisulfate, bitartrate, borate, bromide, butyrate, calcium, calcium edetate, campylate (camphorsulfonate ), Carbonate, chloride, choline, citrate, clavulalate, diethanolamine, dihydrochloride, diphosphate, edetate, edisylate (camphorsulfonate), ecylate (ethanesulfonate), Ethylenediamine, Fumarate, Gluceptate (glucoheptonate), Gluconate, Glucuronate, Glutamate, Hexafluorophosphate, Hexylesorcinate, Hydrabamine (N, N'-bis (dehydrate) Loabiethyl) ethylenediamine), hydrobromide, hydrochloride, hydroxynaphthoate, 1-hydroxy-2-naphthoate, 3-hydroxy-2-naphthoate, iodide, isothionate ( 2-hydroxyethanesulfonate), lactate, lactobionate, laurate, lauryl sulfate, lithium, magnesium, maleate, maleate, mandelate, meglumine (1-deoxy-1- (methyl Amino) -D-glucitol), mesylate, methyl bromide, methylnitrate, methylsulfate, mucate, leadylate, nitrate, N-methylglucamine ammonium salt, oleate, oxalate, palmitate, Pamoate (4,4'-methylenebis-3-hydroxy-2-naphthoate or emcarbonate), pantothenate, phosphate, picrate, polygalacturonate, potassium, propionate, p-toluene Sulfonates, salicylates, sodium, stearate, standing Acetate, Succinate, Sulfate, Sulfosaliculate, Suramate, Tannate, Tartrate, Theocate (8-chloro-3,7-dihydro-1,3-dimethyl-1H-purine-2,6 -Dione), triethiodide, tromethamine (2-amino-2- (hydroxymethyl) -1,3-propanediol), valerate and zinc salts.

본 발명의 화합물과 관련하여 사용되는 경우 "유효량"은 대상체에서 mTOR 또는 PI3K의 억제에 효과적인 양이다.When used in connection with a compound of the present invention an "effective amount" is an amount effective for the inhibition of mTOR or PI3K in a subject.

본 발명 내의 일부 화합물은 하나 이상의 키랄 중심을 보유하고, 본 발명은 이러한 화합물의 각각의 분리된 거울상이성질체 및 상기 거울상이성질체의 혼합물을 포함한다. 다중 키랄 중심이 본 발명의 화합물 내에 존재하는 경우, 본 발명은 각각의 조합 및 그의 혼합을 포함한다. 특정한 입체화학 또는 이성질체 형태를 구체적으로 나타내지 않는 한, 구조의 모든 키랄, 부분입체이성질체 및 라세미 형태가 의도된다. 라세미 형태의 분할 또는 광학 활성 출발 물질로부터의 합성에 의한 것과 같은 광학 활성 형태의 제조 방법은 당업계에 잘 알려져 있다. Some compounds within the present invention possess one or more chiral centers, and the present invention encompasses each of the enantiomers of such compounds and mixtures of such enantiomers. Where multiple chiral centers are present in the compounds of the invention, the invention includes each combination and combination thereof. Unless specifically indicated a particular stereochemical or isomeric form, all chiral, diastereomeric and racemic forms of the structure are intended. Methods of preparing optically active forms, such as by cleavage of racemic forms or by synthesis from optically active starting materials, are well known in the art.

본 발명의 화합물은 mTOR 억제 활성을 나타내고, 따라서 mTOR가 역할을 수행하는 비정상적 세포 성장을 억제하기 위해 사용될 수 있다. 따라서, 본 발명의 화합물은 mTOR의 비정상 세포 성장 작용이 관련된 장애, 예컨대 재협착, 아테롬성동맥경화증, 골 장애, 관절염, 당뇨병성 망막병증, 건선, 양성 전립선 비대증, 아테롬성동맥경화증, 염증, 혈관신생, 면역 장애, 췌장염, 신장 질환, 암 등의 치료에 효과적인 것이다. 특히, 본 발명의 화합물은 우수한 암 세포 성장 억제 효과를 보유하고, 암, 바람직하게는 모든 유형 고체 암 및 악성 림프종, 및 특히, 백혈병, 피부암, 방광암, 유방암, 자궁암, 난소암, 전립선암, 폐암, 결장암, 췌장암, 신장암, 위암, 뇌 종양, 진행성 신세포 암종, 급성 림프모구성 백혈병, 악성 흑색종, 연조직 또는 골 육종 등의 치료에 효과적이다.The compounds of the present invention exhibit mTOR inhibitory activity and thus can be used to inhibit abnormal cell growth in which mTOR plays a role. Accordingly, the compounds of the present invention may be used to treat disorders involving abnormal cell growth of mTOR, such as restenosis, atherosclerosis, bone disorders, arthritis, diabetic retinopathy, psoriasis, benign prostatic hyperplasia, atherosclerosis, inflammation, angiogenesis, It is effective in the treatment of immune disorders, pancreatitis, kidney disease and cancer. In particular, the compounds of the present invention possess excellent cancer cell growth inhibitory effects and are effective on cancer, preferably all types of solid and malignant lymphomas, and especially leukemia, skin cancer, bladder cancer, breast cancer, uterine cancer, ovarian cancer, prostate cancer, lung cancer. It is effective in the treatment of colon cancer, pancreatic cancer, kidney cancer, gastric cancer, brain tumor, advanced renal cell carcinoma, acute lymphoblastic leukemia, malignant melanoma, soft tissue or bone sarcoma.

본 발명의 화합물은 PI3 키나제 억제 활성을 나타내고, 따라서 PI3 키나제가 역할을 수행하는 비정상 세포 성장을 억제하기 위해 사용될 수 있다. 따라서, 본 발명의 화합물은 PI3 키나제의 비정상 세포 성장 작용이 관련된 장애, 예컨대 재협착, 아테롬성동맥경화증, 골 장애, 관절염, 당뇨병성 망막병증, 건선, 양성 전립선 비대증, 아테롬성동맥경화증, 염증, 혈관신생, 면역 장애, 췌장염, 신장 질환, 암 등의 치료에 효과적이다. 특히, 본 발명의 화합물은 우수한 암 세포 성장 억제 효과를 보유하고, 암, 바람직하게는 모든 유형의 고체 암 및 악성 림프종, 및 특히, 백혈병, 피부암, 방광암, 유방암, 자궁암, 난소암, 전립선암, 폐암, 결장암, 췌장암, 신장암, 위암, 뇌 종양, 진행성 신세포 암종, 급성 림프모구성 백혈병, 악성 흑색종, 연조직 또는 골 육종 등의 치료에 효과적이다. The compounds of the present invention exhibit PI3 kinase inhibitory activity and thus can be used to inhibit abnormal cell growth in which PI3 kinase plays a role. Accordingly, the compounds of the present invention can be used to treat disorders involving abnormal cell growth of PI3 kinase, such as restenosis, atherosclerosis, bone disorders, arthritis, diabetic retinopathy, psoriasis, benign prostatic hyperplasia, atherosclerosis, inflammation, angiogenesis It is effective in the treatment of immune disorders, pancreatitis, kidney disease and cancer. In particular, the compounds of the present invention possess excellent cancer cell growth inhibitory effects, and have cancer, preferably solid cancers of all types and malignant lymphomas, and in particular leukemia, skin cancer, bladder cancer, breast cancer, uterine cancer, ovarian cancer, prostate cancer, It is effective in the treatment of lung cancer, colon cancer, pancreatic cancer, kidney cancer, gastric cancer, brain tumor, advanced renal cell carcinoma, acute lymphoblastic leukemia, malignant melanoma, soft tissue or bone sarcoma.

치료 용도를 위해, 약리적으로 활성인 화학식 I의 화합물은 표준 및 통상의 기술을 이용하여 필수 활성 성분으로서의 1종 이상의 상기 화합물을 제약상 허용되는 고체 또는 액체 담체와 연합으로 및, 임의로는, 제약상 허용되는 보조제 및 부형제와 함께 포함하는 제약 조성물로서 투여될 것이다.For therapeutic use, the pharmacologically active compound of formula (I) may be used in combination with, optionally, pharmaceutically as a pharmaceutically acceptable solid or liquid carrier, one or more such compounds as essential active ingredients using standard and conventional techniques. It will be administered as a pharmaceutical composition comprising with an acceptable adjuvant and excipient.

본 발명의 제약 조성물은 경구, 비경구 (피하, 근육내, 피내 및 정맥내 포함), 기관지 또는 비강 투여에 적합한 투여 형태를 포함한다. 따라서, 고체 담체가 사용되는 경우, 제제는 정제화되거나, 분말 또는 펠릿 형태로 경질의 젤라틴 캡슐에 담기거나, 또는 트로키 또는 로젠지의 형태일 수 있다. 고체 담체는 결합제, 충전제, 정제화 윤활제, 붕해제, 습윤제 등과 같은 통상적인 부형제를 함유할 수 있다. 정제는 바람직한 경우 통상적인 기술에 의해 필름 코팅될 수 있다. 액체 담체가 사용되는 경우, 제제는 시럽, 에멀젼, 연질 젤라틴 캡슐, 주사용 멸균 비히클, 수성 또는 비수성의 액체 현탁액의 형태일 수 있거나, 또는 사용 전에 물 또는 기타 적절한 비히클로의 재구성을 위한 건조 생성물일 수 있다. 액체 제제는 통상적인 첨가제, 예컨대 현탁화제, 유화제, 습윤제, 비수성 비히클 (식용 오일 포함), 보존제, 및 향미제 및/또는 착색제를 함유할 수 있다. 비경구 투여에 있어서, 비히클은 보통 적어도 대부분 멸균수를 포함하게 되지만, 염수 용액, 글루코스 용액 등을 사용할 수도 있다. 주사가능 현탁액도 또한 사용될 수 있는데, 이 경우에는 통상적인 현탁화제가 사용될 수 있다. 통상적인 보존제, 완충제 등이 비경구용 투여 형태에 첨가될 수도 있다. 직접적으로 비경구 제제 중의 화학식 I의 화합물의 투여가 특히 유용하다. 제약 조성물은 적절한 양의 활성 성분, 즉 본 발명에 따른 화학식 I의 화합물을 함유하는 바람직한 제제에 적절한 통상적인 기술에 의해 제조된다. 예를 들면, 문헌 [Remington: The Science and Practice of Pharmacy, 20th Edition. Baltimore, MD: Lippincott Williams & Wilkins, 2000] 참조. Pharmaceutical compositions of the invention include dosage forms suitable for oral, parenteral (including subcutaneous, intramuscular, intradermal and intravenous), bronchial or nasal administration. Thus, when solid carriers are used, the preparations may be tableted, in hard gelatin capsules in powder or pellet form, or in the form of troches or lozenges. Solid carriers may contain conventional excipients such as binders, fillers, tableting lubricants, disintegrants, wetting agents, and the like. Tablets may be film coated by conventional techniques if desired. If a liquid carrier is used, the preparation may be in the form of syrups, emulsions, soft gelatin capsules, sterile injectable vehicles, aqueous or non-aqueous liquid suspensions, or dry products for reconstitution with water or other suitable vehicle before use. Can be. Liquid formulations may contain conventional additives such as suspending agents, emulsifiers, wetting agents, non-aqueous vehicles (including edible oils), preservatives, and flavoring and / or coloring agents. For parenteral administration, the vehicle usually contains at least mostly sterile water, but saline solutions, glucose solutions, and the like may also be used. Injectable suspensions may also be used, in which case conventional suspending agents may be used. Conventional preservatives, buffers and the like may also be added to the parenteral dosage form. Particularly useful is the administration of the compound of formula I directly in the parenteral preparation. Pharmaceutical compositions are prepared by conventional techniques suitable for the preferred formulation containing the appropriate amount of active ingredient, ie the compound of formula (I) according to the invention. See, eg, Remington: The Science and Practice of Pharmacy, 20th Edition. Baltimore, MD: Lippincott Williams & Wilkins, 2000.

치료 효과를 달성하기 위한 화학식 I의 화합물의 투여량은 환자의 연령, 체중 및 성별, 및 투여 방식과 같은 그러한 인자에 의존적일 뿐만 아니라, 또한 관련된 특정 장애 또는 질환에 활용되는 특정 화합물의 효능 및 목적하는 칼륨 채널 활성화 활성 정도에도 의존적일 것이다. 또한, 특정 화합물의 처리 및 투여량이 단위 투여 형태로 투여될 수 있고, 따라서 당업자가 상대적인 활성 수준을 반영하기 위해 단위 투여 형태를 조정할 것이 또한 예상된다. 사용될 구체적인 투여량 (및 하루에 투여되는 횟수)에 대한 결정은 의사의 재량권에 속하며, 목적하는 치료 효과를 얻기 위해 본 발명의 구체적인 상황에 대한 투여량의 적정에 의해 달라질 수 있다.The dosage of the compound of formula (I) to achieve a therapeutic effect is not only dependent on such factors as the patient's age, weight and sex, and mode of administration, but also the efficacy and purpose of the particular compound utilized for the particular disorder or disease involved. It will also depend on the degree of potassium channel activation activity. In addition, the treatment and dosage of a particular compound may be administered in unit dosage forms, and therefore it is also contemplated for a person skilled in the art to adjust the unit dosage form to reflect relative levels of activity. Determination of the specific dosage (and frequency administered per day) to be used is within the discretion of the physician and can be varied by titration of dosage for the specific situation of the present invention to obtain the desired therapeutic effect.

본원에 기재된 바와 같은 어떠한 상태로 고통받거나 또는 고통받을 수 있는 인간을 비롯한 포유동물을 위한 화학식 I의 화합물 또는 제약 조성물의 적합한 투여량은 활성 성분 약 0.01 mg/체중 kg 내지 10 mg/체중 kg이다. 비경구 투여에 있어서, 용량은 정맥내 투여를 위해 0.1 mg/체중 kg 내지 1 mg/체중 kg의 범위일 수 있다. 경구 투여에 있어서, 용량은 약 0.1 mg/체중 kg 내지 5 mg/체중 kg일 수 있다. 활성 성분은 바람직하게는 하루에 1 내지 4회로 동일 용량으로 투여될 것이다. 그러나, 통상적으로 적은 투여량을 투여하고, 치료 하의 숙주에 대한 최적의 투여량이 결정될 때까지 투여량을 점차 증가시킨다.Suitable dosages of the compounds of formula (I) or pharmaceutical compositions for mammals, including humans, who may or may suffer from any condition as described herein, are from about 0.01 mg / kg body weight to 10 mg / kg body weight of active ingredient. For parenteral administration, the dose may range from 0.1 mg / kg body weight to 1 mg / kg body weight for intravenous administration. For oral administration, the dose may be about 0.1 mg / kg body weight to 5 mg / kg body weight. The active ingredient will preferably be administered in the same dose 1 to 4 times a day. Typically, however, small doses are administered and the dose is gradually increased until the optimal dose for the host under treatment is determined.

그러나, 화합물의 실제 투여량은 치료할 상태, 투여되는 화합물의 선택, 선택된 투여 경로, 개별 환자의 연령, 체중 및 반응, 및 환자 증상의 중증도를 비롯한 관련 상황에 비추어 의사에 의해 결정될 것이라는 것을 이해할 것이다. However, it will be understood that the actual dosage of the compound will be determined by the physician in light of the relevant circumstances including the condition to be treated, the choice of compound administered, the route of administration chosen, the age, weight and response of the individual patient, and the severity of the patient's symptoms.

본 발명의 화합물 또는 그의 제약상 허용되는 염의 양은 대상체에서 mTOR 또는 PI3K의 억제에 효과적이다. 또한, 시험관내 또는 생체내 검정은 임의로 최적 투여량 범위를 확인하는 것을 돕기 위해 임의로 사용할 수 있다. 사용될 정확한 용량은 또한 투여 경로, 상태, 치료되는 상태의 심각도, 및 치료받는 개체와 관련된 다양한 물리적 요소에 따라 좌우될 수 있고, 건강관리 진료의의 판단에 따라 결정될 수 있다. 동일한 투여량을 약 매 2 시간, 약 매 6 시간, 약 매 8 시간, 약 매 12 시간, 약 매 24 시간, 약 매 36 시간, 약 매 48 시간, 약 매 72 시간, 약 매주, 약 매 2주, 약 매 3주, 약 매달, 및 약 매 2달의 시간 주기를 비롯한 (이에 한정되지는 않음) 다양한 시간 주기로 투여될 수 있다. 요법의 완성 코스에 해당하는 투여 횟수 및 빈도는 건강관리 진료의의 판단에 따라 결정될 것이다. 본원 기술된 유효 투여량은 투여되는 총량을 지칭하고; 즉, 하나 초과의 본 발명의 화합물 또는 그의 제약상 허용되는 염을 투여하는 경우, 유효 투여량은 투여되는 총량에 상응한다.The amount of a compound of the present invention or a pharmaceutically acceptable salt thereof is effective for the inhibition of mTOR or PI3K in a subject. In addition, in vitro or in vivo assays may optionally be used to help identify optimal dosage ranges. The exact dose to be used may also depend on the route of administration, the condition, the severity of the condition being treated, and various physical factors associated with the individual being treated, and may be determined at the discretion of the healthcare practitioner. The same dosage is about every 2 hours, about every 6 hours, about every 8 hours, about every 12 hours, about every 24 hours, about every 36 hours, about every 48 hours, about every 72 hours, about every week, about every 2 hours It can be administered at various time periods, including but not limited to weekly, about every three weeks, about monthly, and about every two months. The frequency and frequency of dosing corresponding to the completion course of therapy will be determined by the healthcare practitioner. Effective dosages described herein refer to the total amount administered; In other words, when administering more than one compound of the present invention or a pharmaceutically acceptable salt thereof, the effective dose corresponds to the total amount administered.

한 실시양태에서, 본 발명의 화합물 또는 그의 제약상 허용되는 염은 또다른 치료제와 동시에 투여된다. In one embodiment, the compound of the present invention or a pharmaceutically acceptable salt thereof is administered simultaneously with another therapeutic agent.

한 실시양태에서, 유효량의 본 발명의 화합물 또는 그의 제약상 허용되는 염 및 유효량의 또다른 치료제를 동일한 조성물 내에 포함하는 조성물이 투여될 수 있다. In one embodiment, a composition can be administered comprising an effective amount of a compound of the invention or a pharmaceutically acceptable salt thereof and an effective amount of another therapeutic agent in the same composition.

다른 치료제의 유효량은 당업자들에게 잘 공지되어 있다. 그러나, 다른 치료제의 최적의 유효량 범위를 결정하는 것은 당업자의 범위 내에 있다. 본 발명의 화합물 또는 그의 제약상 허용되는 염 및 다른 치료제는 부가적으로 작용할 수 있거나, 또는 한 실시양태에서, 상승작용적으로 작용할 수 있다. 본 발명의 한 실시양태에서, 또다른 치료제가 동물에 투여되는 경우, 유효량의 본 발명의 화합물 또는 그의 제약상 허용되는 염은 다른 치료제가 투여되지 않는 경우에서의 그의 유효량 미만으로 투여된다. 이 경우에, 이론에 한정되지 않지만, 본 발명의 화합물 또는 그의 제약상 허용되는 염 및 다른 치료제는 상승작용적으로 작용하는 것으로 여겨진다.Effective amounts of other therapeutic agents are well known to those skilled in the art. However, it is within the scope of those skilled in the art to determine the optimum effective amount range for other therapeutic agents. The compounds of the present invention or their pharmaceutically acceptable salts and other therapeutic agents may additionally act or, in one embodiment, act synergistically. In one embodiment of the invention, when another therapeutic agent is administered to the animal, an effective amount of a compound of the invention or a pharmaceutically acceptable salt thereof is administered at less than its effective amount when no other therapeutic agent is administered. In this case, although not limited to theory, it is believed that the compounds of the present invention or pharmaceutically acceptable salts thereof and other therapeutic agents act synergistically.

화학식 I의 화합물의 제조에 유용한 방법은 하기 실시예에서 설명되고, 반응식 1 내지 3에서 일반화된다:Methods useful for the preparation of compounds of formula (I) are described in the Examples below and are generalized in Schemes 1-3:

반응식 1:Scheme 1:

당업자는 반응식 1 내지 3이 화학식 I의 다른 화합물 및 본 발명에 따른 화학식 I의 화합물의 제약상 허용되는 염을 제조하기 위해 적용될 수 있다는 것을 인지할 것이다. Those skilled in the art will appreciate that Schemes 1 to 3 can be applied to prepare other compounds of formula (I) and pharmaceutically acceptable salts of compounds of formula (I) according to the invention.

하기 약어를 본원에 사용하고, 이들은 하기 나타낸 정의를 갖는다: ACN은 아세토니트릴이고, AcOH는 아세트산이고, ATP는 아데노신 트리포스페이트이고, CHAPS는 3[(3-콜아미도프로필)디메틸암모니오]-프로판술폰산이고, DEAD는 디에틸 아조디카르복실레이트이고, DIAD는 디이소프로필 아조디카르복실레이트이고, DMAP는 디메틸 아미노피리딘이고, DMF는 N,N-디메틸포름아미드이고, DMF-DMA는 디메틸포름아미드 디메틸 아세탈이고, DMSO는디메틸술폭시드이다. 다우썸(Dowtherm)™은 비페닐 (C12H10) 및 디페닐 옥시드 (C12H10O)의 공융 혼합물이다. 다우썸™은 다우 코닝 코퍼레이션의 등록 상표명이다. DPBS는 둘베코 인산염 완충 염수 제제이고, EDTA는 에틸렌디아민테트라아세트산이고, ESI는 전자분무 이온화를 나타내고, EtOAc는 에틸 아세테이트이고, EtOH는 에탄올이고, HEPES는 4-(2-히드록시에틸)-1-피페라진에탄술폰산이고, GMF는 글라스이고, 휘니그 염기는 디이소프로필에틸아민이고, HPLC는 고압 액체 크로마토그래피이고, LPS는 리포폴리사카라이드이고, MeCN은 아세토니트릴이고, MeOH는 메탄올이고, MS는 질량 분석법이고, NEt3은 트리에틸아민이고, NMR은 핵 자기 공명이고, PBS는 포스페이트-완충 염수 (pH 7.4)이고, RPMI 1640은 완충액 (시그마-알드리히 코포레이션, 미국 미주리즈 세인트 루이스 소재)이고, SDS는 도데실 술페이트 (나트륨 염)이고, SRB는 술포로다민 B이고, TBSCl은 tert-부틸디메틸실릴 클로라이드이고, TCA는 트리클로로아세트산이고, TFA는 트리플루오로아세트산이고, THF는 테트라히드로푸란이고, TLC은 박층 크로마토그래피이고, TRIS는 트리스(히드록시메틸)아미노메탄이다.The following abbreviations are used herein and they have the definitions shown below: ACN is acetonitrile, AcOH is acetic acid, ATP is adenosine triphosphate, and CHAPS is 3 [(3-colamidopropyl) dimethylammonio]- Propanesulfonic acid, DEAD is diethyl azodicarboxylate, DIAD is diisopropyl azodicarboxylate, DMAP is dimethyl aminopyridine, DMF is N, N-dimethylformamide, DMF-DMA is dimethyl Formamide dimethyl acetal and DMSO is dimethyl sulfoxide. Dowtherm ™ is a eutectic mixture of biphenyl (C 12 H 10 ) and diphenyl oxide (C 12 H 10 O). Dowsome ™ is a registered trademark of Dow Corning Corporation. DPBS is a Dulbecco phosphate buffered saline formulation, EDTA is ethylenediaminetetraacetic acid, ESI represents electrospray ionization, EtOAc is ethyl acetate, EtOH is ethanol, HEPES is 4- (2-hydroxyethyl) -1 Piperazineethanesulfonic acid, GMF is glass, Hunig's base is diisopropylethylamine, HPLC is high pressure liquid chromatography, LPS is lipopolysaccharide, MeCN is acetonitrile, MeOH is methanol, MS is mass spectrometry, NEt 3 is triethylamine, NMR is nuclear magnetic resonance, PBS is phosphate-buffered saline (pH 7.4), RPMI 1640 is buffer (Sigma-Aldrich Corp., St. Louis, Missouri, USA) Material), SDS is dodecyl sulfate (sodium salt), SRB is sulfodadamine B, TBSCl is tert-butyldimethylsilyl chloride, TCA is trichloroacetic acid, TFA is triple And Oro acid, THF is tetrahydrofuran, TLC is thin layer chromatography, TRIS is tris (hydroxymethyl) amino methane.

방법Way

하기 방법은 화학식 I의 화합물의 합성을 요약하였다. 하기 실시예는 본 발명의 특정 실시양태를 설명하기 위해 제시되지만, 본 발명의 범주를 제한하는 것으로서 해석되지 않아야 한다. The following method summarizes the synthesis of a compound of formula (I). The following examples are presented to illustrate certain embodiments of the invention, but should not be construed as limiting the scope of the invention.

실시예 1: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조Example 1: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea

단계 1: 2-클로로-4,6-디-모르폴린-4-일-[1,3,5]트리아진의 제조:Step 1: Preparation of 2-chloro-4,6-di-morpholin-4-yl- [1,3,5] triazine:

아세톤 (100 ml) 및 부순 얼음 (500 g) 중 시아누르산 클로라이드 (18.4 g, 10 mmol)의 교반 용액에 트리에틸아민 (30.0 g, 과량) 및 모르폴린 (17.4 g, 20 mmol)의 혼합물을 -10℃에서 첨가하였다. 첨가 후에, 반응 혼합물을 실온에서 및 1 시간 동안 교반하고, 물 50 ml로 희석시켰다. 분리된 백색 고체를 여과하고, 물로 세척하였다. 백색 고체를 건조시키고 여과하였다. 조 생성물은 순수한 것으로 밝혀졌고, 다음 단계에 정제 없이 사용하였다. 수율: 25 g, 87％; (M+H) 286.7To a stirred solution of cyanuric chloride (18.4 g, 10 mmol) in acetone (100 ml) and crushed ice (500 g) was added a mixture of triethylamine (30.0 g, excess) and morpholine (17.4 g, 20 mmol). Add at -10 ° C. After addition, the reaction mixture was stirred at rt and for 1 h and diluted with 50 ml of water. The separated white solid was filtered off and washed with water. The white solid was dried and filtered. The crude product was found to be pure and used without purification in the next step. Yield: 25 g, 87%; (M + H) 286.7

단계 2: 4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린의 제조Step 2: Preparation of 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline

2-클로로-4,6-디-모르폴린-4-일-[1,3,5]트리아진 (1.4 g, 4.9 mmol), 촉매량의 테트라키스(트리페닐포스핀)팔라듐(0) (70 mg, 0.061 mmol), 탄산나트륨 용액 2 M (3 mL), 4-아미노페닐보론산 피나콜 에스테르 (1.6 g, 7.3 mmol) 및 DME (100 mL)의 혼합물을 24 시간 동안 환류시켰다. 용매를 증발시키고, 잔류물을 메틸렌 클로라이드 중에 용해시키고, 셀라이트™를 통해 여과하였다. 여과물을 물 (200 mL)로 세척하고, 유기층을 황산마그네슘으로 건조시켰다. 이것을 여과하고, 용매를 증발시켰다. 잔류물을 실리카겔 컬럼 크로마토그래피로 정제하고, 에틸 아세테이트/헥산 (1:1)으로 용리하여 4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 1.40 g (83％ 수율)을 무정형 고체로서 수득하였다. (M+H) 343.2-chloro-4,6-di-morpholin-4-yl- [1,3,5] triazine (1.4 g, 4.9 mmol), catalytic amount of tetrakis (triphenylphosphine) palladium (0) (70 mg, 0.061 mmol), sodium carbonate solution 2M (3 mL), 4-aminophenylboronic acid pinacol ester (1.6 g, 7.3 mmol) and DME (100 mL) were refluxed for 24 h. The solvent was evaporated and the residue was dissolved in methylene chloride and filtered through Celite ™. The filtrate was washed with water (200 mL) and the organic layer was dried over magnesium sulfate. It was filtered and the solvent was evaporated. The residue was purified by silica gel column chromatography and eluted with ethyl acetate / hexanes (1: 1) 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl 1.40 g (83% yield) of aniline were obtained as an amorphous solid. (M + H) 343.

단계 3: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조Step 3: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea

메틸렌 클로라이드 (80 mL) 중 4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.20 g 0.40 mmol)의 혼합물에 0℃에서 트리포스겐 (0.25 mg, 0.84 mmol) 및 트리에틸아민 (3 mL)을 첨가하였다. 혼합물을 20 분 동안 0℃에서 교반하고, 4-아미노 피리딘 (0.10 g 0.83 mmol)을 반응 혼합물에 첨가하고, 추가 2 시간 동안 실온에서 교반하였다. 용매를 증발시키고, 잔류물을 아세토니트릴/TFA를 이동상으로서 사용하는 HPLC에 적용하여 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아 98.2 mg (36％ 수율)을 수득하였다. (M+H) = 463.3.Triphosgene at 0 ° C. in a mixture of 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.20 g 0.40 mmol) in methylene chloride (80 mL) (0.25 mg, 0.84 mmol) and triethylamine (3 mL) were added. The mixture was stirred at 0 ° C. for 20 minutes, 4-amino pyridine (0.10 g 0.83 mmol) was added to the reaction mixture and stirred for another 2 hours at room temperature. The solvent was evaporated and the residue was subjected to HPLC using acetonitrile / TFA as mobile phase to give 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazine-2- Il) phenyl] -3-pyridin-4-ylurea was obtained 98.2 mg (36% yield). (M + H) = 463.3.

아릴 이소시아네이트를 사용한 우레아의 제조를 위한 절차 A:Procedure A for the preparation of urea using aryl isocyanates:

메틸렌 클로라이드 100 (mL) 중 4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (140 mg, 0.40 mmol) 및 촉매량의 디메틸아미노피리딘 (DMAP)의 교반된 혼합물에 약간 과량의 아릴 이소시아네이트 (0.61 mmol)를 첨가하였다. 혼합물을 실온에서 48 시간 동안 교반하였다. 반응 혼합물을 그의 원래 부피의 절반으로 농축시키고, 분리된 침전물을 여과에 의해 수집하고, 메탄올 (15 ml) 및 이어서 디에틸 에테르로 세척하였다. 일부 경우에, 생성물의 극성에 따라, 수득한 조 생성물을 적절한 용매로 용리하는 실리카겔 컬럼 크로마토그래피로 정제하였다.4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (140 mg, 0.40 mmol) in methylene chloride 100 (mL) and catalytic amount of dimethylaminopyridine ( To the stirred mixture of DMAP) was added slightly excess aryl isocyanate (0.61 mmol). The mixture was stirred at rt for 48 h. The reaction mixture was concentrated to half its original volume and the separated precipitate was collected by filtration and washed with methanol (15 ml) and then with diethyl ether. In some cases, depending on the polarity of the product, the crude product obtained was purified by silica gel column chromatography eluting with a suitable solvent.

절차 A에 따라 하기 화합물을 제조하였다:The following compounds were prepared following Procedure A:

실시예 2: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-3-일우레아의 제조Example 2: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-3-ylurea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.08 g 0.23 mmol) 및 3-피리딜 이소시아네이트 (30 mg, 0.25 mmol)로부터 출발하여, 표제 화합물을 백색 고체로서 단리하였다. 생성물을 10％ MeOH:에틸 아세테이트로 용리하는 실리카겔 컬럼 크로마토그래피로 정제하였다. 수율; 60 mg (56％); (M+H)= 463.5.Starting from 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.08 g 0.23 mmol) and 3-pyridyl isocyanate (30 mg, 0.25 mmol) The title compound was isolated as a white solid. The product was purified by silica gel column chromatography eluting with 10% MeOH: ethyl acetate. yield; 60 mg (56%); (M + H) = 463.5.

실시예 3: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-페닐우레아의 제조Example 3: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-phenylurea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (140 mg, 0.40 mmol) 및 페닐 이소시아네이트 (72 mg, 0.61 mmol)로부터 출발하여, 표제 화합물을 백색 고체로서 단리하였다. 생성물을 에틸 아세테이트로 용리하는 실리카겔 컬럼 크로마토그래피로 정제하였다. 수율: 0.128 g (68％) (M+H) = 462.3Starting from 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (140 mg, 0.40 mmol) and phenyl isocyanate (72 mg, 0.61 mmol), The title compound was isolated as a white solid. The product was purified by silica gel column chromatography eluting with ethyl acetate. Yield: 0.128 g (68%) (M + H) = 462.3

실시예 4: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-티오펜-2-일우레아의 제조Example 4: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-thiophen-2-ylurea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (60 mg, 0.17 mmol) 및 2-티에닐 이소시아네이트 (18 mg, 0.14 mmol)로부터 출발하여, 5％ 에틸 아세테이트:메탄올로 용리하는 실리카겔 컬럼 크로마토그래피 후에, 표제 화합물을 회색 고체로서 단리하였다. 수율: 12 mg (14％); (M+H) = 470.From 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (60 mg, 0.17 mmol) and 2-thienyl isocyanate (18 mg, 0.14 mmol) Starting, after silica gel column chromatography eluting with 5% ethyl acetate: methanol, the title compound was isolated as a gray solid. Yield: 12 mg (14%); (M + H) = 470.

실시예 5: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-메틸페닐)우레아의 제조Example 5: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-methylphenyl) urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140 g 0.40 mmol) 및 4-메틸페닐 이소시아네이트 (74 mg, 0.56 mmol)로부터 출발하여, 표제 화합물을 백색 고체로서 단리하였다. 수율; 65 mg (33％) (M+H)= 476.4Starting from 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140 g 0.40 mmol) and 4-methylphenyl isocyanate (74 mg, 0.56 mmol) The title compound was isolated as a white solid. yield; 65 mg (33%) (M + H) = 476.4

실시예 6: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-플루오로페닐)우레아의 제조Example 6: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-fluorophenyl) urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140 g 0.40 mmol) 및 4-플루오로페닐 이소시아네이트 (83 mg, 0.61 mmole)로부터 출발하여, 표제 생성물 65 mg (33％ 수율)을 백색 고체로서 단리하였다. (M+H) = 480.3From 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140 g 0.40 mmol) and 4-fluorophenyl isocyanate (83 mg, 0.61 mmole) Starting, 65 mg (33% yield) of the title product were isolated as a white solid. (M + H) = 480.3

실시예 7: 1-(2,4-디메톡시페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-우레아의 제조Example 7: 1- (2,4-dimethoxyphenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl]- Manufacture of urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140 g 0.40 mmol) 및 2,4-디메톡시페닐 이소시아네이트 (131 mg, 0.73 mmol)로부터 출발하여, 표제 화합물을 백색 고체로서 단리하였다. 수율; 76 mg (36％); (M+H)= 522.44- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140 g 0.40 mmol) and 2,4-dimethoxyphenyl isocyanate (131 mg, 0.73 mmol Starting from), the title compound was isolated as a white solid. yield; 76 mg (36%); (M + H) = 522.4

실시예 8: 1-(4-클로로페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-우레아의 제조Example 8: Preparation of 1- (4-chlorophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140 g 0.40 mmol) 및 4-클로로페닐 이소시아네이트 (94 mg, 0.61 mmol)로부터 출발하여, 표제 화합물을 백색 고체로서 단리하였다. 수율; 60 mg (30％); (M+H)= 496.3Starting from 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140 g 0.40 mmol) and 4-chlorophenyl isocyanate (94 mg, 0.61 mmol) The title compound was isolated as a white solid. yield; 60 mg (30%); (M + H) = 496.3

실시예 9: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-메톡시페닐)우레아의 제조Example 9: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-methoxyphenyl) urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140 g 0.40 mmol) 및 4-메톡시페닐 이소시아네이트 (91 mg, 0.63 mmol)로부터 출발하여, 표제 화합물을 백색 고체로서 단리하였다. 수율; 48 mg (24％); (M+H)= 492.3From 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140 g 0.40 mmol) and 4-methoxyphenyl isocyanate (91 mg, 0.63 mmol) Starting, the title compound was isolated as a white solid. yield; 48 mg (24%); (M + H) = 492.3

실시예 10: (4-클로로페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조Example 10 Preparation of (4-chlorophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140 g 0.40 mmol) 및 4-클로로페닐 이소시아네이트 (94 mg, 0.61 mmol)로부터 출발하여, 표제 화합물을 백색 고체로서 단리하였다. 수율; 60 mg (30％); (M+H)= 496.3Starting from 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140 g 0.40 mmol) and 4-chlorophenyl isocyanate (94 mg, 0.61 mmol) The title compound was isolated as a white solid. yield; 60 mg (30%); (M + H) = 496.3

실시예 11: (2,4-디플루오로페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조Example 11: of (2,4-difluorophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea Produce

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.105 g 0.30 mmol) 및 2,4-디플루오로페닐 이소시아네이트 (71 mg, 0.45 mmol)로부터 출발하여, 표제 화합물을 백색 고체로서 단리하였다. 수율; 40 mg (27％); (M+H)= 498.64- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.105 g 0.30 mmol) and 2,4-difluorophenyl isocyanate (71 mg, 0.45 mmol), the title compound was isolated as a white solid. yield; 40 mg (27%); (M + H) = 498.6

실시예 12: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-에틸우레아의 제조Example 12 Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-ethylurea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.130 g 0.38 mmol) 및 에틸 이소시아네이트 (260 mg, 10배 과량)로부터 출발하여, 표제 화합물을 백색 고체로서 단리하였다. 수율; 38 mg (25％); (M+H)= 414.4Starting from 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.130 g 0.38 mmol) and ethyl isocyanate (260 mg, 10 fold excess), The title compound was isolated as a white solid. yield; 38 mg (25%); (M + H) = 414.4

실시예 13: tert-부틸 3-{[4-(4-{[(4-플루오로페닐)카르바모일]-아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트의 제조Example 13: tert-butyl 3-{[4- (4-{[(4-fluorophenyl) carbamoyl] -amino} phenyl) -6-morpholin-4-yl-1,3,5- Preparation of Triazine-2-yl] amino} azetidine-1-carboxylate

단계 1: 2,4-디클로로-6-모르폴린-4-일-[1,3,5]트리아진의 제조:Step 1: Preparation of 2,4-dichloro-6-morpholin-4-yl- [1,3,5] triazine:

아세톤 (100 ml) 및 부순 얼음 (500 g) 중 시아누르산 클로라이드 (18.4 g, 10 mmol)의 교반 용액에, 트리에틸아민 (30.0 g, 과량) 및 모르폴린 (8.7 g, 10 mmol)의 혼합물을 -10℃에서 첨가하였다. 첨가 후에, 반응 혼합물을 실온에서 및 1 시간 동안 교반하고, 물 50 ml로 희석하였다. 분리된 백색 고체를 여과하고, 물로 세척하였다. 백색 고체를 건조시키고 여과하였다. 조 생성물은 순수한 것으로 밝혀졌고, 다음 단계에 정제 없이 사용하였다. 수율: 18 g, 76％; (M+H) 236.4A mixture of triethylamine (30.0 g, excess) and morpholine (8.7 g, 10 mmol) in a stirred solution of cyanuric chloride (18.4 g, 10 mmol) in acetone (100 ml) and crushed ice (500 g) Was added at -10 ° C. After addition, the reaction mixture was stirred at rt and for 1 h and diluted with 50 ml of water. The separated white solid was filtered off and washed with water. The white solid was dried and filtered. The crude product was found to be pure and used without purification in the next step. Yield: 18 g, 76%; (M + H) 236.4

단계 2: tert-부틸 3-(4-클로로-6-모르폴린-1,3,5-트리아진-2-2-일아미노)아제티딘-1-카르복실레이트의 제조Step 2: Preparation of tert-butyl 3- (4-chloro-6-morpholine-1,3,5-triazin-2-2-ylamino) azetidine-1-carboxylate

아세톤 (50 ml) 및 부순 얼음 중 2,4-디클로로-6-모르폴린-4-일-[1,3,5]트리아진 (2.35 g, 10 mmol)의 교반 용액에, 트리에틸아민 및 1-boc-3-(아미노)아제티딘의 혼합물 (1.72 g)을 서서히 첨가하였다. 반응 혼합물을 실온에서 6 시간 동안 교반하고, 분리된 고체를 여과하였다. 생성물을 건조시키고, 다음 단계에 정제 없이 사용하였다. 수율: 3.0 g (81％); (M+H) 373To a stirred solution of 2,4-dichloro-6-morpholin-4-yl- [1,3,5] triazine (2.35 g, 10 mmol) in acetone (50 ml) and crushed ice, triethylamine and 1 A mixture of -boc-3- (amino) azetidine (1.72 g) was added slowly. The reaction mixture was stirred at rt for 6 h and the separated solid was filtered off. The product was dried and used without purification in the next step. Yield: 3.0 g (81%); (M + H) 373

단계 3: tert-부틸-3-4-(4-(4-아미노페닐)-6-모르폴린-1,3,5-트리아진-2-일아미노)아제티딘-1-카르복실레이트의 제조Step 3: Preparation of tert-butyl-3-4- (4- (4-aminophenyl) -6-morpholine-1,3,5-triazin-2-ylamino) azetidine-1-carboxylate

tert-부틸 3-(4-클로로-6-모르폴린-1,3,5-트리아진-2-2-일아미노)아제티딘-1-카르복실레이트 (1.1 g, 3.0 mmol), 촉매량의 테트라키스(트리페닐포스핀)팔라듐(0) (70 mg, 0061 mmol), 탄산나트륨 용액 2 M (3 mL), 4-아미노페닐보론산 피나콜 에스테르 (0.97 g, 4.5 mmol), DME (100 mL)의 혼합물을 24 시간 동안 환류시켰다. 용매를 증발시키고, 잔류물을 메틸렌 클로라이드 중에 용해시키고, 셀라이트™를 통해 여과하였다. 유기층을 물 (200 mL)로 세척하고, 황산마그네슘 상에서 건조시켰다. 이것을 여과하고, 용매를 증발시켰다. 잔류물을 에틸 아세테이트/헥산 (1:1)을 용리액으로서 사용하여 실리카겔 컬럼 상에서 크로마토그래프하여 tert-부틸-3-4-(4-(4-아미노페닐)-6-모르폴린-1,3,5-트리아진-2-일아미노)아제티딘-1-카르복실레이트 0.86 g (68％ 수율)을 수득하였다. (M+H) 428tert-butyl 3- (4-chloro-6-morpholine-1,3,5-triazin-2-2-ylamino) azetidine-1-carboxylate (1.1 g, 3.0 mmol), catalytic amount tetra Kis (triphenylphosphine) palladium (0) (70 mg, 0061 mmol), sodium carbonate solution 2M (3 mL), 4-aminophenylboronic acid pinacol ester (0.97 g, 4.5 mmol), DME (100 mL) The mixture of was refluxed for 24 hours. The solvent was evaporated and the residue was dissolved in methylene chloride and filtered through Celite ™. The organic layer was washed with water (200 mL) and dried over magnesium sulfate. It was filtered and the solvent was evaporated. The residue was chromatographed on a silica gel column using ethyl acetate / hexanes (1: 1) as eluent to give tert-butyl-3-4- (4- (4-aminophenyl) -6-morpholine-1,3, 0.86 g (68% yield) of 5-triazin-2-ylamino) azetidine-1-carboxylate was obtained. (M + H) 428

단계 4: tert-부틸 3-{[4-(4-{[(4-플루오로페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트의 제조Step 4: tert-butyl 3-{[4- (4-{[(4-fluorophenyl) carbamoyl] amino} phenyl) -6-morpholin-4-yl-1,3,5-triazine -2-yl] amino} azetidine-1-carboxylate

tert-부틸 3-{[4-(4-아미노페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트 (100 mg, 0.23 mmol), 4-플루오로페닐이소시아네이트 (63 mg, 0.46 mmol) 및 DMAP (5 mg)의 혼합물을 실온에서 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 백색 고체; 수율 40 mg (30％); (M+H) 565.6tert-butyl 3-{[4- (4-aminophenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] amino} azetidine-1-carboxylate (100 mg, 0.23 mmol), 4-fluorophenylisocyanate (63 mg, 0.46 mmol) and DMAP (5 mg) were stirred at rt for 24 h. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. White solid; Yield 40 mg (30%); (M + H) 565.6

실시예 14: tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(페닐카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트의 제조Example 14 tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(phenylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) Preparation of Amino] azetidine-1-carboxylate

표제 화합물을 tert-부틸 3-{[4-(4-아미노페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트 (140 mg, 0.32 mmol), 페닐이소시아네이트 (58 mg, 0.49 mmol) 및 DMAP (5 mg)로부터 출발하여 제조하고, 실온에서 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 백색 고체; 수율 40 mg (31％); (M+H) 547.6The title compound is called tert-butyl 3-{[4- (4-aminophenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] amino} azetidine-1-carboxyl Prepared starting from the rate (140 mg, 0.32 mmol), phenylisocyanate (58 mg, 0.49 mmol) and DMAP (5 mg) and stirred at room temperature for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. White solid; Yield 40 mg (31%); (M + H) 547.6

실시예 15: tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-3-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트의 제조Example 15 tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-3-ylcarbamoyl) amino] phenyl} -1,3,5-triazine- Preparation of 2-yl) amino] azetidine-1-carboxylate

표제 화합물을 tert-부틸 3-{[4-(4-아미노페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트 (140 mg, 0.32 mmol), 3-피리딜이소시아네이트 (70 mg, 0.58 mmol) 및 DMAP (5 mg)로부터 출발하여 제조하고, 실온에서 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 백색 고체; 수율 40 mg (23％); (M+H) 548.7.The title compound is called tert-butyl 3-{[4- (4-aminophenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] amino} azetidine-1-carboxyl Prepared starting from the rate (140 mg, 0.32 mmol), 3-pyridylisocyanate (70 mg, 0.58 mmol) and DMAP (5 mg) and stirred at room temperature for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. White solid; Yield 40 mg (23%); (M + H) 548.7.

실시예 16: tert-부틸 3-{[4-(4-{[(4-메틸페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트의 제조Example 16: tert-butyl 3-{[4- (4-{[(4-methylphenyl) carbamoyl] amino} phenyl) -6-morpholin-4-yl-1,3,5-triazine- Preparation of 2-yl] amino} azetidine-1-carboxylate

표제 화합물을 tert-부틸 3-{[4-(4-아미노페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트 (130 mg, 0.27 mmol), 4-톨릴 이소시아네이트 (40 mg, 0.30 mmol) 및 DMAP (5 mg)로부터 출발하여 제조하고, 실온에서 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 백색 고체; 수율 85 mg (47％); (M+H) 561.6.The title compound is called tert-butyl 3-{[4- (4-aminophenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] amino} azetidine-1-carboxyl Prepared starting from the rate (130 mg, 0.27 mmol), 4-tolyl isocyanate (40 mg, 0.30 mmol) and DMAP (5 mg) and stirred at room temperature for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. White solid; Yield 85 mg (47%); (M + H) 561.6.

실시예 17: 1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-페닐우레아의 제조Example 17 1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-phenyl Manufacture of urea

DCM (20 ml) 중 tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(페닐카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트 30 mg (0.055 mmol)의 교반 용액에 TFA (1.5 ml)를 실온에서 첨가하고, 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 수율: 20 (83％); (M+H) 447.Tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(phenylcarbamoyl) amino] phenyl} -1,3,5-triazine-2- in DCM (20 ml) To a stirring solution of 30 mg (0.055 mmol) of amino) azetidine-1-carboxylate, TFA (1.5 ml) was added at room temperature and stirred for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. Yield: 20 (83%); (M + H) 447.

실시예 18: 1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조Example 18 1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridine Preparation of -3-ylurea

DCM (20 ml) 중 tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-3-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트 30 mg (0.055 mmol)의 교반 용액에 TFA (1.5 ml)를 실온에서 첨가하고, 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 수율: 21 (83％); (M+H) 448.5.Tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-3-ylcarbamoyl) amino] phenyl} -1,3,5-tri in DCM (20 ml) To a stirred solution of 30 mg (0.055 mmol) of azin-2-yl) amino] azetidine-1-carboxylate was added TFA (1.5 ml) at room temperature and stirred for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. Yield: 21 (83%); (M + H) 448.5.

실시예 19: 1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-플루오로페닐)우레아의 제조Example 19: 1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- ( Preparation of 4-fluorophenyl) urea

DCM (20 ml) 중 tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(4-플루오로-페닐카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트 30 mg (0.053 mmol)의 교반 용액에 TFA (1.5 ml)를 실온에서 첨가하고, 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 수율: 20 (83％); (M+H) 465.5.Tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(4-fluoro-phenylcarbamoyl) amino] phenyl} -1,3,5- in DCM (20 ml) To a stirring solution of 30 mg (0.053 mmol) of triazin-2-yl) amino] azetidine-1-carboxylate TFA (1.5 ml) was added at room temperature and stirred for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. Yield: 20 (83%); (M + H) 465.5.

실시예 20: 1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-메틸페닐)우레아의 제조Example 20 1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- ( Preparation of 4-methylphenyl) urea

DCM (20 ml) 중 tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(4-메틸-페닐카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트 130 mg (0.23 mmol)의 교반 용액에 TFA (1.5 ml)를 실온에서 첨가하고, 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 수율: 40 (37％); (M+H) 461.5.Tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(4-methyl-phenylcarbamoyl) amino] phenyl} -1,3,5-tri in DCM (20 ml) To a stirred solution of 130 mg (0.23 mmol) of azin-2-yl) amino] azetidine-1-carboxylate was added TFA (1.5 ml) at room temperature and stirred for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. Yield: 40 (37%); (M + H) 461.5.

실시예 21: tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트의 제조Example 21 tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazine- Preparation of 2-yl) amino] azetidine-1-carboxylate

DCM (100 ml) 중 tert-부틸 3-{[4-(4-아미노페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트 (200 mg, 0.47 mmol)의 교반 용액에 0℃에서 트리포스겐 (300 mg) 및 트리에틸아민 (3 ml)을 서서히 첨가하였다. 반응 혼합물을 15 분 동안 교반하고, 4-아미노피리딘 (200 mg. 2.1 mmol)을 첨가하였다. 반응 혼합물을 실온에서 24 시간 동안 교반하고 농축시켰다. 이것을 냉수로 켄칭하고, 분리된 고체를 여과하고, 물로 세척하였다. 이것을 건조시키고 길슨 HPLC로 정제하였다. 수율 100 mg (40％); (M+H) 548.6Tert-butyl 3-{[4- (4-aminophenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] amino} azetidine-1 in DCM (100 ml) To the stirred solution of carboxylate (200 mg, 0.47 mmol) was added slowly triphosphene (300 mg) and triethylamine (3 ml) at 0 ° C. The reaction mixture was stirred for 15 minutes and 4-aminopyridine (200 mg. 2.1 mmol) was added. The reaction mixture was stirred at rt for 24 h and concentrated. It was quenched with cold water and the separated solid was filtered off and washed with water. It was dried and purified by Gilson HPLC. Yield 100 mg (40%); (M + H) 548.6

실시예 22: 1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 22 1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridine Preparation of -4-ylurea

DCM (20 ml) 중 tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트 40 mg (0.073 mmol)의 교반 용액에 TFA (1.5 ml)를 실온에서 첨가하고, 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 수율: 26 (81％); (M+H) 448.5.Tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-tri in DCM (20 ml) To a stirred solution of 40 mg (0.073 mmol) of azin-2-yl) amino] azetidine-1-carboxylate was added TFA (1.5 ml) at room temperature and stirred for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. Yield: 26 (81%); (M + H) 448.5.

실시예 23: 1-{4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-페닐우레아의 제조Example 23 1- {4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine -2-yl] phenyl} -3-phenylurea

단계 1: 3-(4-클로로-6-모르폴린-4-일-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄의 제조Step 1: Preparation of 3- (4-chloro-6-morpholin-4-yl-1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane

2,4-디클로로-6-모르폴린-4-일-[1,3,5]트리아진 (1.5 g, 6.5 mmol)의 교반된 아세톤/부순 얼음 현탁액에, 8-옥사-3-아자비시클로[3.2.1]옥탄 (980 mg, 6.5 mmol) 및 트리에틸아민 (3 ml)을 첨가하고, 실온에서 6 시간 동안 교반하였다. 그 말미에, 분리된 고체를 여과하고, 물로 세척하였다. 조 생성물은 추가 전환을 위해 충분히 순수한 것으로 밝혀졌다. 수율: 2.0 g (99％); mp. 118; (M+H) 313.1To a stirred acetone / crushed ice suspension of 2,4-dichloro-6-morpholin-4-yl- [1,3,5] triazine (1.5 g, 6.5 mmol), 8-oxa-3-azabicyclo [ 3.2.1] octane (980 mg, 6.5 mmol) and triethylamine (3 ml) were added and stirred at rt for 6 h. At the end, the separated solid was filtered off and washed with water. The crude product was found to be sufficiently pure for further conversion. Yield: 2.0 g (99%); mp. 118; (M + H) 313.1

단계 2: 4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]아닐린의 제조Step 2: 4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl ] Production of Aniline

3-(4-클로로-6-모르폴린-4-일-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄 (2.0 g, 6.4 mmol), 촉매량의 테트라키스(트리페닐포스핀)팔라듐(0) (100 mg), 탄산나트륨 용액 2 M (5 mL), 4-아미노페닐보론산 피나콜 에스테르 (1.5 g, 6.43 mmol), DME (200 mL)의 혼합물을 24 시간 동안 환류시켰다. 용매를 증발시키고, 잔류물을 메틸렌 클로라이드 중에 용해시키고, 셀라이트™를 통해 여과하였다. 유기층을 물 (200 mL)로 세척하고, 황산마그네슘 상에서 건조시켰다. 이것을 여과하고, 용매를 증발시켰다. 잔류물을 에틸 아세테이트/헥산 (1:1)을 용리액으로서 사용하는 실리카겔 컬럼 상에서 크로마토그래프하여 표제 생성물 1.4 g (59％ 수율)을 수득하였다. mp. 154; (M+H) 369.4.3- (4-chloro-6-morpholin-4-yl-1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane (2.0 g, 6.4 mmol ), Catalytic amount of tetrakis (triphenylphosphine) palladium (0) (100 mg), sodium carbonate solution 2M (5 mL), 4-aminophenylboronic acid pinacol ester (1.5 g, 6.43 mmol), DME (200 mL) was refluxed for 24 h. The solvent was evaporated and the residue was dissolved in methylene chloride and filtered through Celite ™. The organic layer was washed with water (200 mL) and dried over magnesium sulfate. It was filtered and the solvent was evaporated. The residue was chromatographed on a silica gel column using ethyl acetate / hexanes (1: 1) as eluent to afford 1.4 g (59% yield) of the title product. mp. 154; (M + H) 369.4.

단계 3: 1-{4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-페닐우레아의 제조Step 3: 1- {4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine- Preparation of 2-yl] phenyl} -3-phenylurea

표제 화합물을 4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]아닐린 (120 mg, 0.32 mmol), 페닐이소시아네이트 (80 mg, 0.67 mmol) 및 DMAP (5 mg)로부터 출발하여 제조하고, 실온에서 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 백색 고체; mp: 242; 수율 35 mg (28％); (M+H) 488.56The title compound is 4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl ] Starting from aniline (120 mg, 0.32 mmol), phenylisocyanate (80 mg, 0.67 mmol) and DMAP (5 mg) and stirring at room temperature for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. White solid; mp: 242; Yield 35 mg (28%); (M + H) 488.56

실시예 24: 1-(4-플루오로페닐)-3-{4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 24 1- (4-fluorophenyl) -3- {4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl] phenyl} urea

표제 화합물을 4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]아닐린 (100 mg, 0.27 mmol), 4-플루오로페닐이소시아네이트 (50 mg, 0.36 mmol) 및 DMAP (5 mg)로부터 출발하여 제조하고, 실온에서 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 백색 고체; mp: 248; 수율 86 mg (86％); (M+H) 506.4The title compound is 4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl ] Derived from aniline (100 mg, 0.27 mmol), 4-fluorophenylisocyanate (50 mg, 0.36 mmol) and DMAP (5 mg) and stirred at room temperature for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. White solid; mp: 248; Yield 86 mg (86%); (M + H) 506.4

실시예 25: 1-(4-메틸페닐)-3-{4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 25 1- (4-Methylphenyl) -3- {4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl)- Preparation of 1,3,5-triazin-2-yl] phenyl} urea

표제 화합물을 4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]아닐린 (100 mg, 0.27 mmol), 4-톨릴이소시아네이트 (60 mg, 0.45 mmol) 및 DMAP (5 mg)로부터 출발하여 제조하고, 실온에서 24 시간 동안 교반하였다. 그 말미에, 반응 혼합물을 농축시키고, ACN/물 및 TFA를 사용하여 길슨 HPLC로 정제하였다. 백색 고체; mp: 228; 수율 80 mg (80％); (M+H) 502.4The title compound is 4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl ] Prepared from aniline (100 mg, 0.27 mmol), 4-tolylisocyanate (60 mg, 0.45 mmol) and DMAP (5 mg) and stirred at room temperature for 24 hours. At the end, the reaction mixture was concentrated and purified by Gilson HPLC using ACN / water and TFA. White solid; mp: 228; Yield 80 mg (80%); (M + H) 502.4

실시예 25에 요약된 절차에 따라, 실시예 26 내지 32에 기재된 화합물을 제조하였다.Following the procedure outlined in Example 25, the compounds described in Examples 26-32 were prepared.

실시예 26: 1-[4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)페닐]-3-메틸우레아 (M+H) 452.53Example 26 1- [4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazin-2-yl) phenyl] 3-Methylurea (M + H) 452.53

실시예 27: 2-히드록시에틸 [4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)페닐]카르바메이트 (M+H) 483.54Example 27: 2-hydroxyethyl [4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazin-2-yl ) Phenyl] carbamate (M + H) 483.54

실시예 28: 1-[4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)페닐]-3-[4-(4-메틸피페라진-1-일)페닐]우레아 (M+H) 612.8Example 28 1- [4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (4-methylpiperazin-1-yl) phenyl] urea (M + H) 612.8

실시예 29: 1-[4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)페닐]-3-에틸우레아 (M+H) 466.56Example 29: 1- [4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazin-2-yl) phenyl] 3-ethylurea (M + H) 466.56

실시예 30: 1-시클로프로필-3-[4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)페닐]우레아 (M+H) 478.55Example 30 1-cyclopropyl-3- [4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazine-2 -Yl) phenyl] urea (M + H) 478.55

실시예 31: 1-[4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아 (M+H) 515Example 31: 1- [4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazin-2-yl) phenyl] 3-Pyridin-4-ylurea (M + H) 515

실시예 32: 1-[4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아 (M+H) 544.6Example 32 1- [4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl] urea (M + H) 544.6

실시예 33: 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린의 제조Example 33: 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5-triazine-2- Production of Aniline

단계 1: 4-(4,6-디클로로-1,3,5-트리아진-2-일)모르폴린의 합성Step 1: Synthesis of 4- (4,6-dichloro-1,3,5-triazin-2-yl) morpholine

CH2Cl2 (150 mL) 중 시아누르산 클로라이드 (2.5 g, 13.5 mmol)의 용액에 모르폴린 (1.14 g, 13.5 mmol)을 -78℃에서 적가한 다음, Et3N (3.0 mL, 21.5 mmol)을 첨가하였다. 생성된 반응 혼합물을 -78℃에서 20 분 동안 교반한 후에, CH2Cl2로 희석하였다. 유기상을 물 및 염수로 세척하고, MgSO4 상에서 건조시켰다. 용매를 진공 하에 제거하여 표제 화합물을 백색 결정질 고체로서 수득하였다 (3.027 g, 95％ 수율). MS(ESI) m/z 235.1.To a solution of cyanuric chloride (2.5 g, 13.5 mmol) in CH 2 Cl 2 (150 mL) was added dropwise morpholine (1.14 g, 13.5 mmol) at −78 ° C., followed by Et 3 N (3.0 mL, 21.5 mmol). ) Was added. The resulting reaction mixture was stirred at −78 ° C. for 20 minutes and then diluted with CH 2 Cl 2 . The organic phase was washed with water and brine and dried over MgSO 4 . The solvent was removed in vacuo to afford the title compound as a white crystalline solid (3.027 g, 95% yield). MS (ESI) m / z 235.1.

단계 2: 8-(4-클로로-6-모르폴리노-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3,2,1]옥탄의 합성Step 2: Synthesis of 8- (4-chloro-6-morpholino-1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3,2,1] octane

CH2Cl2 (100 mL) 중 4-(4,6-디클로로-1,3,5-트리아진-2-일)모르폴린 (2.34 g, 10 mmol)의 용액에 3-옥사-8-아자비시클로[3,2,1]옥탄 히드로클로라이드 (1.645 g, 11 mmol) 및 Et3N (4.2 mL, 30 mmol)을 첨가하였다. 혼합물을 실온에서 밤새 교반하였다. 반응 혼합물을 물 및 염수로 세척하고, MgSO4 상에서 건조시켰다. 용매를 진공 하에 제거하여 표제 화합물을 백색 고체로서 수득하였다 (3.0 g, 96％ 수율). MS(ESI) m/z 312.1.3-oxa-8-azabi in a solution of 4- (4,6-dichloro-1,3,5-triazin-2-yl) morpholine (2.34 g, 10 mmol) in CH 2 Cl 2 (100 mL) Cyclo [3,2,1] octane hydrochloride (1.645 g, 11 mmol) and Et 3 N (4.2 mL, 30 mmol) were added. The mixture was stirred at room temperature overnight. The reaction mixture was washed with water and brine and dried over MgSO 4 . The solvent was removed in vacuo to afford the title compound as a white solid (3.0 g, 96% yield). MS (ESI) m / z 312.1.

단계 3: 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린의 합성Step 3: 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5-triazin-2-yl ] Synthesis of aniline

10 mL 바이알에 8-(4-클로로-6-모르폴리노-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3,2,1]옥탄 (311 mg, 1.0 mmol), 4-아미노페닐보론산 피나콜 에스테르 (328 mg, 1.5 mmol), Pd(PPh3)4 (58 mg, 5 mol％), 1,2-디메톡시에탄 (DME, 2.5 mL) 및 2M Na2CO3 수용액 (1.5 mL)을 첨가하였다. 생성된 혼합물을 130℃에서 30 분 동안 마이크로파 오븐에서 가열하였다. 반응 혼합물을 실온으로 냉각시켰다. 수성상을 EtOAc로 추출하고, 합한 유기상을 (MgSO4) 상에서 건조시켰다. 용매를 감압하에 제거하고, 잔류물을 HPLC 분리에 적용하여 표제 화합물을 회백색 고체로서 수득하였다 (280 mg, 76％ 수율). MS(ESI) m/z 369.2.8- (4-chloro-6-morpholino-1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3,2,1] octane (311 mg) in a 10 mL vial , 1.0 mmol), 4-aminophenylboronic acid pinacol ester (328 mg, 1.5 mmol), Pd (PPh 3 ) 4 (58 mg, 5 mol%), 1,2-dimethoxyethane (DME, 2.5 mL) And 2M Na 2 CO 3 aqueous solution (1.5 mL). The resulting mixture was heated at 130 ° C. for 30 minutes in a microwave oven. The reaction mixture was cooled to room temperature. The aqueous phase was extracted with EtOAc and the combined organic phases were dried over (MgSO 4 ). The solvent was removed under reduced pressure and the residue was subjected to HPLC separation to give the title compound as an off white solid (280 mg, 76% yield). MS (ESI) m / z 369.2.

실시예 34: 1-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 34 1- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5-triazine -2-yl] phenyl} -3-pyridin-4-ylurea

CHCl3 (1 mL) 중 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol)의 용액에 Et3N (25 mL, 0.18 mmol) 및 트리포스겐 (18 mg, 0.06 mmol)을 첨가하였다. 혼합물을 실온에서 15 분 동안 교반하고, 4-아미노피리딘 (17 mg, 0.18 mmol)을 첨가하였다. 혼합물을 실온에서 밤새 교반하였다. 용매를 제거하고, 잔류물을 HPLC 분리에 적용하여 표제 화합물을 회백색 고체로서 수득하였다 (1TFA 염, 8.8 mg, 24％ 수율). MS(ESI) m/z 489.2.4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5-triazine in CHCl 3 (1 mL) Et 3 N (25 mL, 0.18 mmol) and triphosgene (18 mg, 0.06 mmol) were added to a solution of -2-yl] aniline (22 mg, 0.06 mmol). The mixture was stirred at rt for 15 min and 4-aminopyridine (17 mg, 0.18 mmol) was added. The mixture was stirred at room temperature overnight. The solvent was removed and the residue was subjected to HPLC separation to give the title compound as off white solid (1TFA salt, 8.8 mg, 24% yield). MS (ESI) m / z 489.2.

실시예 35: 4-[({4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조Example 35: 4-[({4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Preparation of Triazine-2-yl] phenyl} carbamoyl) amino] benzamide

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 4-아미노벤즈아미드 (25 mg, 0.18 mmol)를 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (10.6 mg, 33％ 수율). MS(ESI) m/z 531.2.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgene (18 mg, 0.06 mmol) and 4-aminobenzamide (25 mg, 0.18 mmol) were reacted to give the title compound as an off-white solid ( 10.6 mg, 33% yield). MS (ESI) m / z 531.2.

실시예 36: 1-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조Example 36: 1- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5-triazine -2-yl] phenyl} -3-pyridin-3-ylurea

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 3-아미노피리딘 (17 mg, 0.18 mmol)을 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (1TFA 염, 14.8 mg, 41％ 수율). MS(ESI) m/z 489.5.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgene (18 mg, 0.06 mmol) and 3-aminopyridine (17 mg, 0.18 mmol) were reacted to give the title compound as off-white solid (1TFA). Salt, 14.8 mg, 41% yield). MS (ESI) m / z 489.5.

실시예 37: 1-(4-플루오로페닐)-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 37: 1- (4-fluorophenyl) -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl ) -1,3,5-triazin-2-yl] phenyl} urea

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 4-플루오로아닐린 (20 mg, 0.18 mmol)을 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (14.8 mg, 49％ 수율). MS(ESI) m/z 506.5.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgene (18 mg, 0.06 mmol) and 4-fluoroaniline (20 mg, 0.18 mmol) were reacted to give the title compound as off-white solid ( 14.8 mg, 49% yield). MS (ESI) m / z 506.5.

실시예 38: 1-[4-(히드록시메틸)페닐]-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 38: 1- [4- (hydroxymethyl) phenyl] -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct- Preparation of 8-yl) -1,3,5-triazin-2-yl] phenyl} urea

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 4-아미노벤질 알콜 (22 mg, 0.18 mmol)을 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (9.6 mg, 31％ 수율). MS(ESI) m/z 518.5.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgen (18 mg, 0.06 mmol) and 4-aminobenzyl alcohol (22 mg, 0.18 mmol) were reacted to give the title compound as an off-white solid ( 9.6 mg, 31% yield). MS (ESI) m / z 518.5.

실시예 39: 1-[4-(2-히드록시에틸)페닐]-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 39: 1- [4- (2-hydroxyethyl) phenyl] -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] Preparation of Oct-8-yl) -1,3,5-triazin-2-yl] phenyl} urea

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 4-아미노펜에틸 알콜 (24 mg, 0.18 mmol)을 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (10.6 mg, 33％ 수율). MS(ESI) m/z 532.5.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgene (18 mg, 0.06 mmol) and 4-aminophenethyl alcohol (24 mg, 0.18 mmol) were reacted to give the title compound as an off-white solid ( 10.6 mg, 33% yield). MS (ESI) m / z 532.5.

실시예 40: 2-(디에틸아미노)에틸 4-[({4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트의 제조Example 40 2- (diethylamino) ethyl 4-[({4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl ) -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 프로카인 히드로클로라이드 (50 mg, 0.18 mmol)를 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (1TFA 염, 14.6 mg, 33％ 수율). MS(ESI) m/z 613.6.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgene (18 mg, 0.06 mmol) and procaine hydrochloride (50 mg, 0.18 mmol) were reacted to give the title compound as off-white solid (1TFA). Salt, 14.6 mg, 33% yield). MS (ESI) m / z 613.6.

실시예 41: 1-(4-메틸페닐)-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 41 1- (4-methylphenyl) -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl)- Preparation of 1,3,5-triazin-2-yl] phenyl} urea

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 p-톨루이딘 (20 mg, 0.18 mmol)을 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (9.2 mg, 31％ 수율). MS(ESI) m/z 502.5.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgene (18 mg, 0.06 mmol) and p-toluidine (20 mg, 0.18 mmol) were reacted to give the title compound as an off-white solid (9.2 mg). , 31% yield). MS (ESI) m / z 502.5.

실시예 42: 1-(4-시아노페닐)-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 42 1- (4-cyanophenyl) -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl ) -1,3,5-triazin-2-yl] phenyl} urea

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 4-아미노벤조니트릴 (21 mg, 0.18 mmol)을 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (14.3 mg, 46％ 수율). MS(ESI) m/z 513.5.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgen (18 mg, 0.06 mmol) and 4-aminobenzonitrile (21 mg, 0.18 mmol) were reacted to give the title compound as an off-white solid ( 14.3 mg, 46% yield). MS (ESI) m / z 513.5.

실시예 43: 1-[4-(4-메틸피페라진-1-일)페닐]-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 43: 1- [4- (4-methylpiperazin-1-yl) phenyl] -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [ 3.2.1] Oct-8-yl) -1,3,5-triazin-2-yl] phenyl} urea

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 4-(4-메틸피페라진-1-일)아닐린 (54 mg, 0.18 mmol)을 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (2TFA 염, 3.2 mg, 7％ 수율). MS(ESI) m/z 586.6.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgene (18 mg, 0.06 mmol) and 4- (4-methylpiperazin-1-yl) aniline (54 mg, 0.18 mmol) The title compound was obtained as an off-white solid (2TFA salt, 3.2 mg, 7% yield). MS (ESI) m / z 586.6.

실시예 44: 1-이소프로필-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 44 1-isopropyl-3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3 , 5-triazin-2-yl] phenyl} urea

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 이소프로필아민 (11 mg, 0.18 mmol)을 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (13.6 mg, 50％ 수율). MS(ESI) m/z 454.5.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgen (18 mg, 0.06 mmol) and isopropylamine (11 mg, 0.18 mmol) were reacted to give the title compound as an off-white solid (13.6 mg). , 50% yield). MS (ESI) m / z 454.5.

실시예 45: 1-(2-히드록시에틸)-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 45 1- (2-hydroxyethyl) -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl ) -1,3,5-triazin-2-yl] phenyl} urea

실시예 34에 기재된 절차에 따라, 4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]아닐린 (22 mg, 0.06 mmol), 트리포스겐 (18 mg, 0.06 mmol) 및 에탄올아민 (11 mg, 0.18 mmol)을 반응시켜 표제 화합물을 회백색 고체로서 수득하였다 (14.4 mg, 53％ 수율). MS(ESI) m/z 456.5.According to the procedure described in Example 34, 4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -1,3,5- Triazin-2-yl] aniline (22 mg, 0.06 mmol), triphosgene (18 mg, 0.06 mmol) and ethanolamine (11 mg, 0.18 mmol) were reacted to give the title compound as an off-white solid (14.4 mg, 53% yield). MS (ESI) m / z 456.5.

실시예 46: 1-[2-(디메틸아미노)에틸]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아의 제조, MS (ES+) 513.62 (M+H)+Example 46 1- [2- (dimethylamino) ethyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholine Preparation of -4-yl-1,3,5-triazin-2-yl] phenyl} urea, MS (ES +) 513.62 (M + H) &lt; + &gt;

실시예 47: 1-{4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조, MS (ESI) m/z 489.3.Example 47 1- {4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine -2-yl] phenyl} -3-pyridin-3-ylurea, MS (ESI) m / z 489.3.

실시예 48: 1-{4-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조, mp 258℃; MS (ESI) m/z 489.3.Example 48: 1- {4- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine -2-yl] phenyl} -3-pyridin-4-ylurea, mp 258 ° C .; MS (ESI) m / z 489.3.

실시예 1, 단계 3에 요약된 바와 같은 절차에 따라 하기 화합물을 제조하였다.The following compounds were prepared following the procedure as summarized in Example 1, Step 3.

실시예 49: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(2-메틸피리딘-4-일)우레아 MS (ESI) m/z 477.3.Example 49: 1- [4- (4,6-Dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (2-methylpyridin-4-yl) Urea MS (ESI) m / z 477.3.

실시예 50: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(2-히드록시에틸)페닐]우레아 MS (ESI) m/z 506.4.Example 50: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (2-hydroxyethyl) Phenyl] urea MS (ESI) m / z 506.4.

실시예 51: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아.Example 51: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl] Urea.

실시예 52: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(1-히드록시에틸)페닐]우레아 MS (ESI) m/z 506.4.Example 52: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (1-hydroxyethyl) Phenyl] urea MS (ESI) m / z 506.4.

실시예 53: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(트리플루오로메틸)페닐]우레아 MS (ESI) m/z 530.2.Example 53: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (trifluoromethyl) phenyl ] Urea MS (ESI) m / z 530.2.

실시예 54: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-히드록시페닐)우레아 MS (ESI) m/z 478.2.Example 54 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-hydroxyphenyl) urea MS ( ESI) m / z 478.2.

실시예 55: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[5-(트리플루오로메틸)피리딘-2-일]우레아 MS (ESI) m/z 530.5.Example 55 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [5- (trifluoromethyl) pyridine -2-yl] urea MS (ESI) m / z 530.5.

실시예 56: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[2,2,2-트리플루오로-1-히드록시-1-(트리플루오로메틸)에틸]페닐}우레아 MS (ESI) m/z 621.54.Example 56: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4- [2,2,2- Trifluoro-1-hydroxy-1- (trifluoromethyl) ethyl] phenyl} urea MS (ESI) m / z 621.54.

실시예 57: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[3-(1-히드록시에틸)페닐]우레아 MS (ESI) m/z 506.3.Example 57: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [3- (1-hydroxyethyl) Phenyl] urea MS (ESI) m / z 506.3.

실시예 58: 메틸 4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트 MS (ESI) m/z 520.3.Example 58: methyl 4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate MS ( ESI) m / z 520.3.

실시예 59: 1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 59: 1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} Preparation of 3-Pyridin-4-ylurea

단계 1: 무수 THF 중 NaH (50％ 460 mg)의 교반 용액에 테트라히드로-2H-피란-4-올 (1.02 g, 10 mmol)을 실온에서 서서히 첨가하였다. 반응 혼합물을 실온에서 30 분 동안 교반하고, THF (50 ml) 중 2,4-디클로로-6-모르폴린-4-일-[1,3,5]트리아진 (2.35 g, 10 mmol)을 서서히 첨가하였다. 반응 혼합물을 실온에서 48 시간 동안 교반하고, 빙냉수로 서서히 켄칭하였다. 이것을 CHCl3으로 추출하고, 물로 잘 세척하고, 무수 MgSO4 상에서 건조시켰다. 이것을 여과하고 농축시키고, 2-클로로-4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진을 40％ 에틸 아세테이트:헥산으로 용리하는 실리카겔 컬럼 크로마토그래피로 정제하였다. 수율: 1.5 g, 50％; 백색 고체; mp 91℃; MS (ESI) m/z 301.52Step 1: Tetrahydro-2H-pyran-4-ol (1.02 g, 10 mmol) was added slowly to a stirred solution of NaH (50% 460 mg) in dry THF at room temperature. The reaction mixture is stirred at room temperature for 30 minutes and slowly add 2,4-dichloro-6-morpholin-4-yl- [1,3,5] triazine (2.35 g, 10 mmol) in THF (50 ml). Added. The reaction mixture was stirred at rt for 48 h and slowly quenched with ice cold water. It was extracted with CHCl 3 , washed well with water and dried over anhydrous MgSO 4 . It was filtered and concentrated to 2-chloro-4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazine in 40% ethyl acetate: hexane Purification by silica gel column chromatography eluting with. Yield: 1.5 g, 50%; White solid; mp 91 ° C .; MS (ESI) m / z 301.52

단계 2: 4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]아닐린을 실시예 1, 단계 2에 기재된 바와 같은 절차에 따라 제조하였다. 2-클로로-4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진 (1.5 g, 4.9 mmol)로부터 출발하여, 에틸 아세테이트로 용리하는 실리카겔 컬럼 크로마토그래피로 정제한 후에 생성물 980 mg (56％ 수율)을 단리하였다. Mp. 188℃; MS (ESI) m/z 358.2.Step 2: 4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] aniline in Example 1, Prepared according to the procedure as described in step 2. Ethyl acetate starting from 2-chloro-4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazine (1.5 g, 4.9 mmol) After purification by silica gel column chromatography eluting with 980 mg (56% yield) of the product was isolated. Mp. 188 ° C .; MS (ESI) m / z 358.2.

단계 3: 1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아를 실시예 1, 단계 3에 기재된 바와 같은 절차에 따라 제조하였다. 4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]아닐린 (212 mg. 0.59 mmol)으로부터 출발하여 최종 생성물 190 mg (수율, 67％)을 백색 고체로서 단리하였다. mp 238℃; MS (ESI) m/z 478.3.Step 3: 1- {4- [4-Morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl}- 3-pyridin-4-ylurea was prepared following the procedure as described in Example 1, Step 3. From 4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] aniline (212 mg. 0.59 mmol) Starting, 190 mg (yield, 67%) of final product were isolated as a white solid. mp 238 ° C .; MS (ESI) m / z 478.3.

실시예 60: 1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-페닐우레아의 제조Example 60: 1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} Preparation of 3-Phenylurea

1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-페닐우레아는 4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]아닐린 및 상응하는 페닐이소시아네이트를 반응시켜 제조하였다. 생성물을 길슨 HPLC로 정제하였다. MS (ESI) m/z 476.5.1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-phenyl Ureas are 4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] aniline and the corresponding phenylisocyanates It was prepared by reaction. The product was purified by Gilson HPLC. MS (ESI) m / z 476.5.

실시예 61: 1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조Example 61 1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} Preparation of 3-Pyridin-3-ylurea

1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아는 4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]아닐린 및 상응하는 3-피리딜이소시아네이트를 반응시켜 제조하였다. 생성물을 길슨 HPLC로 정제하였다. MS (ESI) m/z 477.53.1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-pyridine -3-ylurea is 4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] aniline and the corresponding Prepared by reacting 3-pyridyl isocyanate. The product was purified by Gilson HPLC. MS (ESI) m / z 477.53.

실시예 62: 1-[4-(히드록시메틸)페닐]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 62: 1- [4- (hydroxymethyl) phenyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1, Preparation of 3,5-triazin-2-yl] phenyl} urea

1-[4-(히드록시메틸)페닐]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아는 실시예 1, 단계 3에 기재된 바와 같은 트리포스겐 절차에 따라 제조하였다. 생성물을 길슨 HPLC로 정제하였다. MS (ESI) m/z 506.6.1- [4- (hydroxymethyl) phenyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5- Triazine-2-yl] phenyl} urea was prepared according to the triphosgen procedure as described in Example 1, Step 3. The product was purified by Gilson HPLC. MS (ESI) m / z 506.6.

실시예 63: 1-(2-메틸피리딘-4-일)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 63 1- (2-methylpyridin-4-yl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1, Preparation of 3,5-triazin-2-yl] phenyl} urea

1-(2-메틸피리딘-4-일)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아는 실시예 1, 단계 3에 기재된 바와 같은 트리포스겐 절차에 따라 제조하였다. 생성물을 길슨 HPLC로 정제하였다. MS (ESI) m/z 491.5.1- (2-methylpyridin-4-yl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5- Triazine-2-yl] phenyl} urea was prepared according to the triphosgen procedure as described in Example 1, Step 3. The product was purified by Gilson HPLC. MS (ESI) m / z 491.5.

실시예 64: 1-[2-(메틸아미노)에틸]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 64 1- [2- (methylamino) ethyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3 , 5-triazin-2-yl] phenyl} urea

1-[2-(메틸아미노)에틸]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아는 실시예 1, 단계 3에 기재된 바와 같은 트리포스겐 절차에 따라 제조하였다. 생성물을 길슨 HPLC로 정제하였다. MS (ESI) m/z 457.54.1- [2- (methylamino) ethyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-tri Azin-2-yl] phenyl} urea was prepared according to the Triphosgen procedure as described in Example 1, Step 3. The product was purified by Gilson HPLC. MS (ESI) m / z 457.54.

실시예 65: 1-(3-아세틸페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 65 1- (3-acetylphenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5- Preparation of Triazine-2-yl] phenyl} urea

1-(3-아세틸페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아는 4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]아닐린 및 상응하는 3-아세틸이소시아네이트를 반응시켜 제조하였다. 생성물을 길슨 HPLC로 정제하였다. MS (ESI) m/z 518.58.1- (3-acetylphenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazine-2 -Yl] phenyl} urea is 4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] aniline and Prepared by reacting the corresponding 3-acetylisocyanate. The product was purified by Gilson HPLC. MS (ESI) m / z 518.58.

실시예 66: 1-[4-(디메틸아미노)페닐]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 66 1- [4- (dimethylamino) phenyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3 , 5-triazin-2-yl] phenyl} urea

1-[4-(디메틸아미노)페닐]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아는 4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]아닐린 및 상응하는 4-(N,N-디메틸아미노)페닐이소시아네이트를 반응시켜 제조하였다. 생성물을 길슨 HPLC로 정제하였다. MS (ESI) m/z 519.61.1- [4- (dimethylamino) phenyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-tri Azin-2-yl] phenyl} urea is 4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl ] Prepared by reacting aniline and the corresponding 4- (N, N-dimethylamino) phenylisocyanate. The product was purified by Gilson HPLC. MS (ESI) m / z 519.61.

실시예 67: 4-[3-{4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐}우레이도]벤조산의 제조Example 67 Preparation of 4- [3- {4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl} ureido] benzoic acid

메틸 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조에이트 (1.4 g, 2.69 mmol), THF (10 mL), MeOH (5 mL) 및 H2O (2.5 mL)의 교반된 혼합물에 LiOH.H2O (339 mg, 8.07 mmol)를 첨가한 후에, 환류 하에 8 시간 동안 교반하였다. 농축시키고 H2O (5 mL)를 첨가한 후에, 2N HCl을 사용하여 산성화시켰다. 고체를 여과하고, H2O로 세척하고 건조시켜 생성물을 황갈색 고체로서 수득하였다 (1.3 g, 96％ 수율); MS (ESI) m/z = 506.3Methyl 4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoate (1.4 g, 2.69 mmol), THF (10 mL), MeOH (5 mL) and H 2 O (2.5 mL) were added LiOH.H 2 O (339 mg, 8.07 mmol) and then stirred under reflux for 8 h. After concentration and H 2 O (5 mL) was added, acidified with 2N HCl. The solid was filtered off, washed with H 2 O and dried to give the product as a tan solid (1.3 g, 96% yield); MS (ESI) m / z = 506.3

실시예 68: N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드의 제조Example 68: N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) urei Fig.) Preparation of Benzamide

NMP 2 mL 중 4-[3-{4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐}우레이도]벤조산 (150 mg; 0.297 mmol), 휘니그 염기 (303 μL, 1.782 mmol), HBTU (563 mg, 1.485 mmol)의 교반 용액을 1 시간 동안 실온에서 교반하고, 여기에 N',N'-디메틸에탄-1,2-디아민 (130 μL, 1.188 mmol)을 첨가한 후에, 밤새 교반하였다. CH2Cl2 (40 mL)를 첨가하고, 포화 NaHCO3 및 H2O로 세척하였다. 농축시키고 MeOH 중 CH2Cl2:MeOH:7N NH3 (10:1:0.22)을 사용하는 실리카겔 크로마토그래피로 정제하여 생성물을 백색 고체로서 수득하였다 (98 mg, 57％ 수율); MS (ESI) m/z = 576.4.4- [3- {4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl} ureido] benzoic acid (150 mg; 0.297 mmol) in 2 mL NMP, Huni The stirred solution of its base (303 μL, 1.782 mmol) and HBTU (563 mg, 1.485 mmol) was stirred for 1 hour at room temperature, and N ', N'-dimethylethane-1,2-diamine (130 μL, 1.188 mmol) was added and then stirred overnight. CH 2 Cl 2 (40 mL) was added and washed with saturated NaHCO 3 and H 2 O. Concentrate and purify by silica gel chromatography using CH 2 Cl 2 : MeOH: 7N NH 3 (10: 1: 0.22) in MeOH to give the product as a white solid (98 mg, 57% yield); MS (ESI) m / z = 576.4.

실시예 68: HCl 염으로서의 N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드의 제조Example 68: N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) as an HCl salt Preparation of Phenyl) ureido) benzamide

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드 (72 mg, 0.125 mmol) 및 MeOH (1 mL)에 디옥산 중 4N HCl (1 mL)을 첨가하고, 3 시간 동안 교반하였다. 고체를 여과하고, 에테르로 세척하여 생성물을 백색 고체로서 수득하였다 (73 mg, 수율 = 95％); MS (ESI) m/z = 576.4.N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzamide (72 mg, 0.125 mmol) and MeOH (1 mL) were added 4N HCl in dioxane (1 mL) and stirred for 3 hours. The solid was filtered off and washed with ether to give the product as a white solid (73 mg, yield = 95%); MS (ESI) m / z = 576.4.

실시예 69: 1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아 히드로클로라이드의 제조Example 69 1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-car Preparation of Bonyl) phenyl) urea Hydrochloride

NMP 2 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (150 mg; 0.297 mmol), 휘니그 염기 (303 μL, 1.782 mmol), HBTU (563 mg, 1.485 mmol)의 교반 용액을 실시예 68에 따라 1-메틸피페라진 (132 μL, 1.188 mmol)과 반응시켜 1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아를 백색 고체로서 수득하였다 (95 mg, 54％ 수율); MS (ESI) m/z = 588.4.4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (150 mg; 0.297 mmol) in 2 mL NMP, Huni The stirred solution of the base (303 μL, 1.782 mmol) and HBTU (563 mg, 1.485 mmol) was reacted with 1-methylpiperazine (132 μL, 1.188 mmol) according to Example 68 to give 1- (4- (4, 6-Dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea was obtained as a white solid ( 95 mg, 54% yield); MS (ESI) m / z = 588.4.

1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아 (70 mg, 0.119 mmol) 및 MeOH (1 mL)에 디옥산 중 4N HCl (1 mL)을 첨가하고, 3 시간 동안 교반하였다. 고체를 여과하고, 에테르로 세척하여 생성물을 백색 고체로서 수득하였다 (74 mg, 수율 = 100％).1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) To urea (70 mg, 0.119 mmol) and MeOH (1 mL) was added 4N HCl in dioxane (1 mL) and stirred for 3 h. The solid was filtered off and washed with ether to give the product as a white solid (74 mg, yield = 100%).

실시예 70: 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드의 제조Example 70 Preparation of 4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N-methylbenzamide

NMP 2 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (150 mg; 0.297 mmol), 휘니그 염기 (303 μL, 1.782 mmol), HBTU (563 mg, 1.485 mmol)의 교반 용액을 실시예 68에 따라 메틸아민 (594 μL, THF 중 2M 용액)과 반응시켜 생성물을 백색 고체로서 수득하였다 (118 mg, 77％ 수율); MS (ESI) m/z = 519.3.4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (150 mg; 0.297 mmol) in 2 mL NMP, Huni A stirred solution of its base (303 μL, 1.782 mmol), HBTU (563 mg, 1.485 mmol) was reacted with methylamine (594 μL, 2M solution in THF) according to Example 68 to give the product as a white solid (118 mg, 77% yield); MS (ESI) m / z = 519.3.

실시예 71: N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드 히드로클로라이드의 제조Example 71 N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) urei Figure 6) Preparation of -N-methylbenzamide hydrochloride

NMP 2 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (150 mg; 0.297 mmol), 휘니그 염기 (303 μL, 1.782 mmol), HBTU (563 mg, 1.485 mmol)의 교반 용액을 실시예 68에 따라 N1,N1,N2-트리메틸에탄-1,2-디아민 (154 μL, 1.188 mmol)과 반응시켜 N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드를 백색 고체로서 수득하였다 (88 mg, 50％ 수율); MS (ESI) m/z = 590.2.4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (150 mg; 0.297 mmol) in 2 mL NMP, Huni A stirred solution of its base (303 μL, 1.782 mmol) and HBTU (563 mg, 1.485 mmol) was reacted with N1, N1, N2-trimethylethane-1,2-diamine (154 μL, 1.188 mmol) according to Example 68. N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido)- N-methylbenzamide was obtained as a white solid (88 mg, 50% yield); MS (ESI) m / z = 590.2.

N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드 (55 mg, 0.127 mmol) 및 MeOH (1 mL)에 디옥산 중 4N HCl (1 mL)를 첨가하고, 3 시간 동안 교반하였다. 고체를 여과하고, 에테르로 세척하여 생성물을 백색 고체로서 수득하였다 (70 mg, 수율 = 88％).N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N To methylbenzamide (55 mg, 0.127 mmol) and MeOH (1 mL) was added 4N HCl in dioxane (1 mL) and stirred for 3 h. The solid was filtered and washed with ether to give the product as a white solid (70 mg, yield = 88%).

실시예 72: 1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-모르폴리노피페리딘-1-카르보닐)페닐)우레아의 제조Example 72: 1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-morpholinopiperidine-1 Preparation of -carbonyl) phenyl) urea

NMP 1 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (50 mg; 0.099 mmol), 휘니그 염기 (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol)의 교반 용액을 실시예 68에 따라 4-(피페리딘-4-일)모르폴린 (67 mg, 0.396 mmol)과 반응시켰다. 용매를 증발시키고, HPLC로 정제하여 생성물을 수득하였다 (40.1 mg, 62％ 수율); MS (ESI) m/z = 658.74- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (50 mg; 0.099 mmol) in 1 mL NMP, Huni A stirred solution of the base (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol) was reacted with 4- (piperidin-4-yl) morpholine (67 mg, 0.396 mmol) according to Example 68. . The solvent was evaporated and purified by HPLC to give the product (40.1 mg, 62% yield). MS (ESI) m / z = 658.7

실시예 73: 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(퀴누클리딘-3-일)벤즈아미드의 제조Example 73: 4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N- (quinuclidin-3- I) Preparation of Benzamide

NMP 2 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (50 mg; 0.099 mmol), 휘니그 염기 (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol)의 용액을 실시예 68에 따라 퀴누클리딘-3-아민 (79 mg, 0.396 mmol)과 반응시켰다. 용매를 증발시키고, HPLC로 정제하여 생성물을 수득하였다 (24.3 mg, 40％ 수율); MS (ESI) m/z = 614.74- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (50 mg; 0.099 mmol) in 2 mL NMP, Huni A solution of its base (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol) was reacted with quinuclidin-3-amine (79 mg, 0.396 mmol) according to Example 68. The solvent was evaporated and purified by HPLC to give the product (24.3 mg, 40% yield); MS (ESI) m / z = 614.7

실시예 74: 1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(피롤리딘-1-일)피페리딘-1-카르보닐)페닐)우레아의 제조Example 74: 1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4- (pyrrolidine-1- I) Preparation of piperidine-1-carbonyl) phenyl) urea

NMP 2 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (50 mg; 0.099 mmol), 휘니그 염기 (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol)의 용액을 실시예 68에 따라 4-[1-피롤리디닐]피페리딘 (61 mg, 0.396 mmol)과 반응시켰다. 용매를 증발시키고, HPLC로 정제하여 생성물을 백색 고체로서 수득하였다 (37 mg, 58％ 수율); MS (ESI) m/z = 642.74- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (50 mg; 0.099 mmol) in 2 mL NMP, Huni A solution of its base (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol) was reacted with 4- [1-pyrrolidinyl] piperidine (61 mg, 0.396 mmol) according to Example 68. The solvent was evaporated and purified by HPLC to give the product as a white solid (37 mg, 58% yield); MS (ESI) m / z = 642.7

실시예 75: 1-(4-(1,4'-비피페리딘-1'-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아의 제조Example 75: 1- (4- (1,4'-bipiperidine-1'-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-tri Preparation of Azin-2-yl) phenyl) urea

NMP 2 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (50 mg; 0.099 mmol), 휘니그 염기 (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol)의 용액을 실시예 68에 따라 1,4'-비피페리딘 (67 mg, 0.396 mmol)과 반응시켰다. 용매를 증발시키고, HPLC로 정제하여 생성물을 백색 고체로서 수득하였다 (39 mg, 60％ 수율); MS (ESI) m/z = 656.8.4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (50 mg; 0.099 mmol) in 2 mL NMP, Huni A solution of its base (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol) was reacted with 1,4′-bipiperidine (67 mg, 0.396 mmol) according to Example 68. The solvent was evaporated and purified by HPLC to give the product as a white solid (39 mg, 60% yield). MS (ESI) m / z = 656.8.

실시예 76: 1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아의 제조Example 76: 1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-tri Preparation of Azin-2-yl) phenyl) urea

NMP 2 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (50 mg; 0.099 mmol), 휘니그 염기 (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol)의 용액을 실시예 68에 따라 N,N-디메틸피페리딘-4-아민 (51 mg, 0.396 mmol)과 반응시켰다. 용매를 증발시키고, HPLC로 정제하여 생성물을 수득하였다 (30.6 mg, 52％ 수율); MS (ESI) m/z = 616.74- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (50 mg; 0.099 mmol) in 2 mL NMP, Huni A solution of its base (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol) was reacted with N, N-dimethylpiperidin-4-amine (51 mg, 0.396 mmol) according to Example 68. The solvent was evaporated and purified by HPLC to give the product (30.6 mg, 52% yield); MS (ESI) m / z = 616.7

실시예 77: 1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아의 제조Example 77: 1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (piperazin-1-carbonyl) phenyl Production of urea

NMP 2 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (50 mg; 0.099 mmol), 휘니그 염기 (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol)의 용액을 실시예 68에 따라 피페라진 (34 mg, 0.396 mmol)과 반응시켰다. 용매를 증발시키고, HPLC로 정제하여 생성물을 수득하였다 (17.2 mg, 30％ 수율); MS (ESI) m/z = 573.64- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (50 mg; 0.099 mmol) in 2 mL NMP, Huni A solution of its base (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol) was reacted with piperazine (34 mg, 0.396 mmol) according to Example 68. The solvent was evaporated and purified by HPLC to give the product (17.2 mg, 30% yield); MS (ESI) m / z = 573.6

실시예 78: 1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(피리딘-2-일)아세틸)페닐)우레아의 제조Example 78: 1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (2- (pyridin-2-yl) Preparation of Acetyl) phenyl) urea

NMP 2 mL 중 4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산 (50 mg; 0.099 mmol), 휘니그 염기 (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol)의 용액을 실시예 68에 따라 피리딘-2-일메탄아민 (43 mg, 0.396 mmol)과 반응시켰다. 용매를 증발시키고, HPLC로 정제하여 생성물을 수득하였다 (9 mg, 15％ 수율); MS (ESI) m/z = 596.6.4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid (50 mg; 0.099 mmol) in 2 mL NMP, Huni A solution of its base (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol) was reacted with pyridin-2-ylmethanamine (43 mg, 0.396 mmol) according to Example 68. The solvent was evaporated and purified by HPLC to give the product (9 mg, 15% yield); MS (ESI) m / z = 596.6.

3-(4,6-디클로로-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄의 제조Preparation of 3- (4,6-dichloro-1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane

아세톤 (20 mL) 및 물 (10 mL) 중 시아누르산 클로라이드 (2.00 g, 10.85 mmol)의 용액에 0℃에서 포화 수성 NaHCO3 (25 mL) 및 아세톤 (25 mL) 중 8-옥사-3-아자비시클로[3.2.1]옥탄 히드로클로라이드 (1.46 g, 9.76 mmol)의 용액을 적하 깔때기를 통해 15 분에 걸쳐 첨가하였다. 반응물을 0℃에서 2 시간 동안 교반한 후에, 여과하여 백색 침전물을 수집하였다. 침전물을 물 (25 mL)로 세척하고 건조시켰다. 조 생성물을 컬럼 크로마토그래피 (헥산 중 30:70 에틸 아세테이트)로 정제하여 3-(4,6-디클로로-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄 (1.55 g)을 백색 고체로서 수득하였다.To a solution of cyanuric chloride (2.00 g, 10.85 mmol) in acetone (20 mL) and water (10 mL) at 0 ° C. 8-oxa-3- in saturated aqueous NaHCO 3 (25 mL) and acetone (25 mL) A solution of azabicyclo [3.2.1] octane hydrochloride (1.46 g, 9.76 mmol) was added over 15 minutes via a dropping funnel. The reaction was stirred at 0 ° C. for 2 hours and then filtered to collect a white precipitate. The precipitate was washed with water (25 mL) and dried. The crude product was purified by column chromatography (30:70 ethyl acetate in hexane) to give 3- (4,6-dichloro-1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [ 3.2.1] octane (1.55 g) was obtained as a white solid.

3-(4-클로로-6-(치환된 아미노)-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄의 제조 절차:Procedure for preparation of 3- (4-chloro-6- (substituted amino) -1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane:

아세톤 (1 mL) 및 물 (1 mL) 중 3-(4,6-디클로로-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄 (0.085 g, 0.33 mmol) 및 Na2CO3 (0.041 g, 0.39 mmol)의 용액에 바람직한 아민 (0.36 mmol)을 첨가하였다. 용액을 55℃로 가열하고, 2 시간 동안 교반한 후에 농축시켜 조 아미노-트리아진을 수득하고, 이것을 정제 없이 바로 사용하였다. 이 절차에 따라, 하기 화합물을 제조하였다.3- (4,6-dichloro-1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane in acetone (1 mL) and water (1 mL) ( To a solution of 0.085 g, 0.33 mmol) and Na 2 CO 3 (0.041 g, 0.39 mmol) was added the desired amine (0.36 mmol). The solution was heated to 55 ° C., stirred for 2 h and then concentrated to give crude amino-triazine, which was used directly without purification. According to this procedure, the following compounds were prepared.

3-(4-클로로-6-(피페리딘-1-일)-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄:3- (4-Chloro-6- (piperidin-1-yl) -1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane:

(310.3, M+H)(310.3, M + H)

3-(4-클로로-6-(피롤리딘-1-일)-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄3- (4-chloro-6- (pyrrolidin-1-yl) -1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane

(296.3, M+H)(296.3, M + H)

t-부틸 2-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-1,3,5-트리아진-2-일아미노)에틸카르바메이트t-butyl 2- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro-1,3,5-triazin-2-ylamino) ethylcarba Mate

(385.3, M+H)(385.3, M + H)

2-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-1,3,5-트리아진-2-일아미노)에탄올2- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro-1,3,5-triazin-2-ylamino) ethanol

(286.3, M+H)(286.3, M + H)

4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-N-페닐-1,3,5-트리아진-2-아민4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro-N-phenyl-1,3,5-triazin-2-amine

(318.3, M+H)(318.3, M + H)

4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-N-시클로헥실-1,3,5-트리아진-2-아민4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro-N-cyclohexyl-1,3,5-triazin-2-amine

(324.3, M+H)(324.3, M + H)

t-부틸 3-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-1,3,5-트리아진-2-일아미노)아제티딘-1-카르복실레이트t-butyl 3- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro-1,3,5-triazin-2-ylamino) azetidine- 1-carboxylate

(397.3, M+H)(397.3, M + H)

4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(치환된 아미노)-1,3,5-트리아진-2-일)아닐린의 제조 방법Preparation of 4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (substituted amino) -1,3,5-triazin-2-yl) aniline Way

마이크로 바이알 내 톨루엔 (2 mL), 에탄올 (2 mL) 및 2M 수성 Na2CO3 (0.700 mL) 중 비스-아미노 트리아진 클로라이드 (0.33 mmol)의 현탁액을 5 분 동안 N2로 살포하였다. Pd(PPh3)4 (0.021 mg, 0.018 mmol) 및 4-아미노페닐보론산 피나콜 에스테르 (0.094 mg, 0.43 mmol)를 첨가하고, 바이알을 밀봉하고, 1 시간 동안 110℃로 가열하였다. 혼합물을 냉각시키고, 셀라이트™를 통해 여과하였다. 필터 케이크를 에틸 아세테이트로 세척하고, 여과물을 염수로 세척하고, 건조시키고, 농축시켰다. 조 물질을 HPLC (워터스 시스템, H2O w/ 0.05％ NH4OH 중 5-70％ CH3CN)로 정제하여 아릴-치환된 트리아진 화합물을 수득하였다. 이 절차에 따라 하기 화합물을 제조하였다.A suspension of bis-amino triazine chloride (0.33 mmol) in toluene (2 mL), ethanol (2 mL) and 2M aqueous Na 2 CO 3 (0.700 mL) in a micro vial was sparged with N 2 for 5 minutes. Pd (PPh 3 ) 4 (0.021 mg, 0.018 mmol) and 4-aminophenylboronic acid pinacol ester (0.094 mg, 0.43 mmol) were added, the vial was sealed and heated to 110 ° C. for 1 hour. The mixture was cooled down and filtered through Celite ™. The filter cake was washed with ethyl acetate and the filtrate was washed with brine, dried and concentrated. The crude material was purified by HPLC (Waters system, H 2 O w / 5-70% CH 3 CN in 0.05% NH 4 OH) to afford aryl-substituted triazine compounds. According to this procedure, the following compounds were prepared.

4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페리딘-1-일)-1,3,5-트리아진-2-일)아닐린 (367.4, M+H)4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (piperidin-1-yl) -1,3,5-triazin-2-yl Aniline (367.4, M + H)

4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피롤리딘-1-일)-1,3,5-트리아진-2-일)아닐린 (353.3, M+H)4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (pyrrolidin-1-yl) -1,3,5-triazin-2-yl Aniline (353.3, M + H)

2-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일아미노)에탄올; (343.3, M+H)2- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -1,3,5-triazin-2-ylamino) ethanol ; (343.3, M + H)

4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-N-페닐-1,3,5-트리아진-2-아민; (375.3, M+H)4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -N-phenyl-1,3,5-triazin-2-amine; (375.3, M + H)

4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-N-시클로헥실-1,3,5-트리아진-2-아민; (381.4, M+H)4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -N-cyclohexyl-1,3,5-triazin-2-amine; (381.4, M + H)

t-부틸 3-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일아미노)아제티딘-1-카르복실레이트; (454.4, M+H).t-butyl 3- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -1,3,5-triazin-2-yl Amino) azetidine-1-carboxylate; (454.4, M + H).

1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(치환된 아미노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조 절차:1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (substituted amino) -1,3,5-triazin-2-yl) Preparation Procedure of Phenyl) -3- (pyridin-4-yl) urea:

CH2Cl2 (1 mL) 중 트리포스겐 (0.034 mg, 0.114 mmol)의 용액을 제조하였다. CH2Cl2 (1 mL) 및 트리에틸아민 (0.095 mL, 0.68 mmol) 중 바람직한 트리아진 아닐린 유도체 (0.23 mmol)의 용액을 첨가하고, 반응물을 실온에서 15 분 동안 교반되도록 하였다. 이어서, THF (1 mL) 중 4-아미노피리딘 (0.043 mg, 0.46 mmol)의 용액을 첨가하고, 용액을 실온에서 3 시간 동안 교반한 후, 농축시키고 HPLC (워터스 시스템, H2O w/ 0.05％ NH4OH 중 5-70％ CH3CN)로 정제하여 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(치환된 아미노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아 유도체를 수득하였다. 이 절차에 따라 하기 화합물을 제조하였다:A solution of triphosgene (0.034 mg, 0.114 mmol) in CH 2 Cl 2 (1 mL) was prepared. A solution of the preferred triazine aniline derivative (0.23 mmol) in CH 2 Cl 2 (1 mL) and triethylamine (0.095 mL, 0.68 mmol) was added and the reaction was allowed to stir at room temperature for 15 minutes. Then a solution of 4-aminopyridine (0.043 mg, 0.46 mmol) in THF (1 mL) is added, the solution is stirred at rt for 3 h, then concentrated and HPLC (Waters system, H 2 O w / 0.05% Purified by 5-70% CH 3 CN in NH 4 OH) to give 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (substituted amino ) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea derivative was obtained. The following compounds were prepared according to this procedure:

실시예 79: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조; 487.2, M+H.Example 79 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (piperidin-1-yl) -1,3,5 Preparation of -triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea; 487.2, M + H.

실시예 80: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피롤리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조; 474.2, M+H.Example 80: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (pyrrolidin-1-yl) -1,3,5 Preparation of -triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea; 474.2, M + H.

실시예 81: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(1- 히드록시에틸)페닐]우레아의 제조Example 81: 1- [4- (4,6-Dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (1-hydroxyethyl) Phenyl] Urea Preparation

메틸렌 클로라이드 중 4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140, 0.40 mmol)의 교반된 혼합물에 0℃에서 트리포스겐 (0.25, 0.84 mmol) 및 Et3N (3 mL)을 첨가하였다. 반응 혼합물을 20 분 동안 0℃에서 교반하였다. 이어서, 1-(4-아미노페닐)에탄올 (0.10 g, 0.73 mmol)을 혼합물에 첨가하였다. 반응 혼합물을 약 16 시간 동안 실온에서 교반하였다. 용매를 제거하였다. 잔류물을 DMSO 중에 용해시키고, 아세토니트릴 완충액 TFA를 사용하여 HPLC에 두어 [4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(1-히드록시에틸)페닐]우레아 48 mg (24％)을 수득하였다. M+H 506.4.To a stirred mixture of 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140, 0.40 mmol) in methylene chloride triphosphene (0.25 , 0.84 mmol) and Et 3 N (3 mL) were added. The reaction mixture was stirred at 0 ° C. for 20 minutes. 1- (4-aminophenyl) ethanol (0.10 g, 0.73 mmol) was then added to the mixture. The reaction mixture was stirred for about 16 hours at room temperature. The solvent was removed. The residue was dissolved in DMSO and placed in HPLC using acetonitrile buffer TFA [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl]- 48 mg (24%) of 3- [4- (1-hydroxyethyl) phenyl] urea were obtained. M + H 506.4.

실시예 82: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(2-메틸피리딘-4-일)우레아의 제조Example 82: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (2-methylpyridin-4-yl) Manufacture of urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140, 0.40 mmol) 및 2-메틸-4-아미노피리딘 (80 mg, 0.73 mmol)으로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(2-메틸피리딘-4-일)우레아를 HPLC 정제로 단리하였다. 수율: 60 mg, 27％; MS (ESI) m/z = 477.3.4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140, 0.40 mmol) and 2-methyl-4-aminopyridine (80 mg, 0.73 mmol 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- according to the procedure outlined in Example 81 (2-methylpyridin-4-yl) urea was isolated by HPLC purification. Yield: 60 mg, 27%; MS (ESI) m / z = 477.3.

실시예 83: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아의 제조Example 83 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl] Manufacture of urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140, 0.40 mmol) 및 4-아미노페닐메탄올 (100 mg, 0.81 mmol)로부터 출발하여 실시예 81에 기재된 절차에 따라, 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)-페닐]우레아를 HPLC 정제로 단리하였다. 수율: 58 mg, 26％; MS (ESI) m/z = 492.3.Starting from 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140, 0.40 mmol) and 4-aminophenylmethanol (100 mg, 0.81 mmol) 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (in accordance with the procedure described in Example 81). Hydroxymethyl) -phenyl] urea was isolated by HPLC purification. Yield: 58 mg, 26%; MS (ESI) m / z = 492.3.

실시예 84: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-히드록시페닐]우레아의 제조Example 84 Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4-hydroxyphenyl] urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140, 0.40 mmol) 및 4-아미노페놀 (89 mg, 0.81 mmol)로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-히드록시페닐]우레아를 HPLC 정제로 단리하였다. 수율: 62 mg, 16％; MS (ESI) m/z = 478.2.Starting from 4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140, 0.40 mmol) and 4-aminophenol (89 mg, 0.81 mmol) 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4-hydride, according to the procedure outlined in Example 81 Roxyphenyl] urea was isolated by HPLC purification. Yield: 62 mg, 16%; MS (ESI) m / z = 478.2.

실시예 85: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(트리플루오로메틸)페닐]우레아의 제조Example 85: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (trifluoromethyl) phenyl ] Manufacture of Urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140, 0.40 mmol) 및 4-트리플루오로메틸아닐린 (100 mg, 0.62 mmol)으로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(트리플루오로메틸)페닐]우레아를 HPLC 정제로 단리하였다. 수율: 25 mg, 13％; MS (ESI) m/z = 430.2.4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140, 0.40 mmol) and 4-trifluoromethylaniline (100 mg, 0.62 mmol) 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [according to the procedure outlined in Example 81 starting from 4- (trifluoromethyl) phenyl] urea was isolated by HPLC purification. Yield: 25 mg, 13%; MS (ESI) m / z = 430.2.

실시예 86: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[2,2,2-트리플루오로-1- 히드록시-1-(트리플루오로메틸)에틸]페닐}우레아의 제조Example 86: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4- [2,2,2- Preparation of Trifluoro-1-hydroxy-1- (trifluoromethyl) ethyl] phenyl} urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.140, 0.40 mmol) 및 4-트리플루오로메틸아닐린 (140 mg, 0.40 mmol)으로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[2,2,2-트리플루오로-1-히드록시-1-(트리플루오로메틸)에틸]페닐}우레아를 HPLC 정제로 단리하였다. 수율: 40 mg, 16％; MS (ESI) m/z = 628.3.4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.140, 0.40 mmol) and 4-trifluoromethylaniline (140 mg, 0.40 mmol) 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {following the procedure outlined in Example 81 4- [2,2,2-trifluoro-1-hydroxy-1- (trifluoromethyl) ethyl] phenyl} urea was isolated by HPLC purification. Yield: 40 mg, 16%; MS (ESI) m / z = 628.3.

실시예 87: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[5-(트리플루오로메틸)피리딘-2-일]우레아의 제조Example 87: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [5- (trifluoromethyl) pyridine -2-yl] production of urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.160, 0.47 mmol) 및 2-아미노-5-트리플루오로페닐피리딘 (100 mg, 0.61 mmol)으로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[5-(트리플루오로메틸)피리딘-2-일]우레아를 HPLC 정제로 단리하였다. 수율: 10 mg, 4.1％; MS (ESI) m/z = 531.3.4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.160, 0.47 mmol) and 2-amino-5-trifluorophenylpyridine (100 mg , 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl], following the procedure outlined in Example 81 starting from -3- [5- (trifluoromethyl) pyridin-2-yl] urea was isolated by HPLC purification. Yield: 10 mg, 4.1%; MS (ESI) m / z = 531.3.

실시예 88: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[3-(1- 히드록시에틸)페닐]우레아의 제조Example 88: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [3- (1-hydroxyethyl) Phenyl] Urea Preparation

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (0.160, 0.47 mmol) 및 1-(3-아미노페닐)에탄올 (100 mg, 0.73 mmol)로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[3-(1-히드록시에틸)페닐]우레아를 HPLC 정제로 단리하였다. 수율: 10 mg, 4.1％; MS (ESI) m/z = 531.3.4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (0.160, 0.47 mmol) and 1- (3-aminophenyl) ethanol (100 mg, 0.73 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3 according to the procedure outlined in Example 81 starting from mmol) -[3- (1-hydroxyethyl) phenyl] urea was isolated by HPLC purification. Yield: 10 mg, 4.1%; MS (ESI) m / z = 531.3.

실시예 89: 1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 89: 1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} Preparation of Phenyl) -3-pyridin-4-ylurea

단계 1: 2-클로로-4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진의 제조:Step 1: Preparation of 2-chloro-4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazine:

메틸렌 클로라이드 200 mL 중 1,3,5-트리아진의 디클로로모노모르폴리노 유도체 (2.0 g, 8.5 mmol)의 교반 용액에 3S-3-메틸모르폴린 (0.85 g, 8.5 mmol)을 첨가하고, 2 당량의 트리에틸아민 1.7 mL와 적하 방식으로 합하였다. 첨가 후에 반응 혼합물을 실온에서 3 시간 동안 교반하고, 물로 켄칭하였다. 수성층을 물로 잘 세척하고, 무수 MgS04 상에서 건조시키고 여과하였다. 용매를 증발시키고, 얻은 잔류물을 디에틸 에테르/헥산 (1:1)으로 연화처리하고 여과하였다. 고체를 추가 정제 없이 사용하였다. (1.0 g, 40％ 수율). M+H 357.3.To a stirred solution of 1,3,5-triazine dichloromonomorpholino derivative (2.0 g, 8.5 mmol) in 200 mL of methylene chloride was added 3S-3-methylmorpholine (0.85 g, 8.5 mmol), 2 Combined dropwise with 1.7 equivalents of triethylamine. After addition the reaction mixture was stirred at rt for 3 h and quenched with water. The aqueous layer was washed well with water, dried over anhydrous MgSO 4 and filtered. The solvent was evaporated and the residue obtained was triturated with diethyl ether / hexanes (1: 1) and filtered. The solid was used without further purification. (1.0 g, 40% yield). M + H 357.3.

단계 2: 4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}아닐린의 제조:Step 2: Preparation of 4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} aniline:

DME (100 mL) 중 2-클로로-4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진 (1.26, 4.2 mmol), 탄산나트륨 용액 (2M, 2 mL), 테트라키스 팔라듐 트리페닐포스핀 70 mg (촉매량) 및 4-아미노페닐 보론산 피나콜 에스테르 (1.37 g, 6.3 mmol)의 혼합물을 24 시간 동안 환류하에 가열하였다. 용매를 증발시키고, 잔류물을 메틸렌 클로라이드 중에 재용해시키고, 셀라이트™를 통해 여과하였다. 용매를 증발시키고, 잔류물을 먼저 26/4 헥산/에틸 아세테이트, 그 다음 1/1 헥산 에틸 아세테이트로 증가시키면서 용리하는 실리카겔 상에서 크로마토그래피하여 4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}아닐린 1.0 (71％ 수율)을 수득하였다; M+H 357.2.2-chloro-4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazine (1.26, 4.2 mmol in DME (100 mL) ), A mixture of sodium carbonate solution (2M, 2 mL), 70 mg (catalyst amount) of tetrakis palladium triphenylphosphine and 4-aminophenyl boronic acid pinacol ester (1.37 g, 6.3 mmol) was heated to reflux for 24 hours. . The solvent was evaporated and the residue was redissolved in methylene chloride and filtered through Celite ™. The solvent was evaporated and the residue was chromatographed on silica gel eluting with increasing first to 26/4 hexanes / ethyl acetate, then 1/1 hexane ethyl acetate to 4- {4-[(3S) -3-methylmorpholine -4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} aniline 1.0 (71% yield) was obtained; M + H 357.2.

단계 3: 1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조:Step 3: 1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl Preparation of 3-Pyridin-4-ylurea:

4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}아닐린 (0.160, 0.44 mmol) 및 4-아미노피리딘 (100 mg, 1.06 mmol)로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아를 HPLC 정제로 단리하였다. 수율: 125 mg, 60％; MS (ESI) m/z 477.3.4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} aniline (0.160, 0.44 mmol) And 1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6, following the procedure outlined in Example 81 starting from 4-aminopyridine (100 mg, 1.06 mmol). -Morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea was isolated by HPLC purification. Yield: 125 mg, 60%; MS (ESI) m / z 477.3.

실시예 90: 1-[4-(2-히드록시에틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아의 제조Example 90: 1- [4- (2-hydroxyethyl) phenyl] -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholine-4- Preparation of 1-1,3,5-triazin-2-yl} phenyl) urea

4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}아닐린 (0.160, 0.44 mmol) 및 4-(1-히드록시에틸)아닐린 (137 mg, 1 mmole)로부터 출발하여 실시예 81에 기재된 절차에 따라, 1-[4-(2-히드록시에틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아를 HPLC 정제로 단리하였다. 수율: 125 mg, 60％; MS (ESI) m/z 519.64- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} aniline (0.160, 0.44 mmol) And 1- [4- (2-hydroxyethyl) phenyl] -3- (4-, starting from 4- (1-hydroxyethyl) aniline (137 mg, 1 mmole) following the procedure described in Example 81 {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea was isolated by HPLC purification. . Yield: 125 mg, 60%; MS (ESI) m / z 519.6

실시예 91: 1-[4-(2-히드록시메틸l)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아의 제조Example 91: 1- [4- (2-hydroxymethyll) phenyl] -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholine-4 Preparation of -yl-1,3,5-triazin-2-yl} phenyl) urea

4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}아닐린 (0.160, 0.44 mmol) 및 4-아미노페닐메탄올 (0.10 g, 0.81 mmol)로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-[4-(2-히드록시메틸l)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아를 HPLC 정제로 단리하였다. 수율: 55 mg, 16％; MS (ESI) m/z 506.3.4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} aniline (0.160, 0.44 mmol) And 1- [4- (2-hydroxymethyll) phenyl] -3- (4- {4-, starting from 4-aminophenylmethanol (0.10 g, 0.81 mmol) and following the procedure outlined in Example 81. [(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea was isolated by HPLC purification. Yield: 55 mg, 16%; MS (ESI) m / z 506.3.

실시예 92: 1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(2-메틸피리딘-4-일)우레아의 제조Example 92: 1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} Preparation of Phenyl) -3- (2-methylpyridin-4-yl) urea

4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}아닐린 (0.160, 0.44 mmol) 및 2-메틸-4-아미노피리딘 (0.10 g, 0.92 mmol)으로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(2-메틸피리딘-4-일)우레아를 HPLC 정제로 단리하였다. 수율: 75 mg, 36％; MS (ESI) m/z 491.3.4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} aniline (0.160, 0.44 mmol) And 1- (4- {4-[(3S) -3-methylmorpholine-4-, following the procedure outlined in Example 81 starting from 2-methyl-4-aminopyridine (0.10 g, 0.92 mmol) Il] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3- (2-methylpyridin-4-yl) urea was isolated by HPLC purification. Yield: 75 mg, 36%; MS (ESI) m / z 491.3.

실시예 93: 1-[4-(1-히드록시에틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아의 제조Example 93: 1- [4- (1-hydroxyethyl) phenyl] -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholine-4- Preparation of 1-1,3,5-triazin-2-yl} phenyl) urea

4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}아닐린 (0.160, 0.44 mmol) 및 1-(4-아미노페닐)에탄올 (126 mg, 0.92 mmol)로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-[4-(1-히드록시에틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아를 HPLC 정제로 단리하였다. MS (ESI) m/z 519.6.4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} aniline (0.160, 0.44 mmol) And 1- [4- (1-hydroxyethyl) phenyl] -3- (4-, starting from 1- (4-aminophenyl) ethanol (126 mg, 0.92 mmol), following the procedure outlined in Example 81. {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea was isolated by HPLC purification. . MS (ESI) m / z 519.6.

실시예 94: 1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조Example 94: of 1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea Produce

단계 1: 무수 THF (50 ml) 중 이소프로판올 (250 mg, 4.1 mmol)의 교반 용액에 -78℃에서 n-부틸리튬 (2.6 ml, 1.6 mol 용액)을 서서히 첨가하였다. 반응 혼합물을 30 분 동안 교반하고, THF 중 2,4-디클로로-6-모르폴린-4-일-[1,3,5]트리아진 (1.00 g, 4.25 mmol)의 용액을 상기 용액에 첨가하였다. 반응 혼합물을 실온에서 24 시간 동안 교반하고, 물로 켄칭하고, DCM으로 추출하였다. 얻어진 조 생성물을 다음 단계에 정제 없이 사용하였다.Step 1: To a stirred solution of isopropanol (250 mg, 4.1 mmol) in dry THF (50 ml) was slowly added n-butyllithium (2.6 ml, 1.6 mol solution) at -78 ° C. The reaction mixture was stirred for 30 minutes and a solution of 2,4-dichloro-6-morpholin-4-yl- [1,3,5] triazine (1.00 g, 4.25 mmol) in THF was added to the solution. . The reaction mixture was stirred at rt for 24 h, quenched with water and extracted with DCM. The crude product obtained was used without purification in the next step.

단계 2: (조) 4-(클로로-6-이소프로폭실-1,2,3-트리아진-2-일)모르폴린 (2.91 g, 11.27 mmol), 4-아미노-페닐보론산 피나콜 에스테르 (3.59 g, 16.4 mmol), 테트라키스 팔라듐 트리페닐포스핀 (120 mg 촉매량) 및 탄산나트륨 용액 (2M, 2 mL)의 혼합물을 DME (100 mL) 중에 24 시간 동안 환류시켰다. 용매를 제거하고, 잔류물을 메틸렌 클로라이드 중에 재용해시키고, 셀라이트™를 통해 여과하였다. 용매를 증발시키고, 잔류물을 먼저 26:4 헥산:에틸 아세테이트, 그 다음 1/1 헥산 에틸 아세테이트로 증가시키면서 용리하여 실리카겔 상에서 크로마토그래피하여 4-(4-이소프로폭시-6-모르폴리노-1,3,5-트리아진-2-일)아닐린 0.65 g (수율 18％)을 수득하였다. M+H 316.3.Step 2: (Cho) 4- (chloro-6-isopropoxyl-1,2,3-triazin-2-yl) morpholine (2.91 g, 11.27 mmol), 4-amino-phenylboronic acid pinacol ester (3.59 g, 16.4 mmol), a mixture of tetrakis palladium triphenylphosphine (120 mg catalytic amount) and sodium carbonate solution (2M, 2 mL) was refluxed in DME (100 mL) for 24 h. The solvent was removed and the residue was redissolved in methylene chloride and filtered through Celite ™. The solvent was evaporated and the residue was first eluted with increasing to 26: 4 hexanes: ethyl acetate, then 1/1 hexane ethyl acetate and chromatographed on silica gel to give 4- (4-isopropoxy-6-morpholino- 0.65 g (18% yield) of 1,3,5-triazin-2-yl) aniline were obtained. M + H 316.3.

단계 3: 4-(4-이소프로폭시-6-모르폴리노-1,3,5-트리아진-2-일)아닐린 (0.140, 0.44 mmol) 및 4-아미노피리딘 (100 mg, 1.06 mmol)으로부터 출발하여 실시예 81에 요약된 절차에 따라, 1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아를 HPLC 정제로 단리하였다. 수율: 15 mg, 7.8％; MS (ESI) m/z = 436.3.Step 3: 4- (4-isopropoxy-6-morpholino-1,3,5-triazin-2-yl) aniline (0.140, 0.44 mmol) and 4-aminopyridine (100 mg, 1.06 mmol) 1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl]-, according to the procedures outlined in Example 81 starting from 3-pyridin-4-ylurea was isolated by HPLC purification. Yield: 15 mg, 7.8%; MS (ESI) m / z = 436.3.

실시예 95: 메틸 4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트의 제조Example 95 Methyl 4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzo Manufacture of Eight

4-(4-이소프로폭시-6-모르폴리노-1,3,5-트리아진-2-일)아닐린 (1.3 g, 4.1 mmol), 트리에틸아민 (2 ml) 및 4-카르보메톡시-페닐이소시아네이트 (1451 mg, 8.2 mmol)의 혼합물을 48 시간 동안 교반하고, 물로 켄칭하고, 잘 세척하였다. 유기층을 건조시키고 여과하였다. 이것을 농축시키고, 먼저 10％ 에틸 아세테이트:헥산으로, 그 후에 40％ 에틸 아세테이트:헥산으로 용리하는 컬럼 크로마토그래피로 정제하였다. 백색 고체; 600 mg, 30％; MS (ESI) m/z 492.5.4- (4-isopropoxy-6-morpholino-1,3,5-triazin-2-yl) aniline (1.3 g, 4.1 mmol), triethylamine (2 ml) and 4-carbomethoxy A mixture of -phenylisocyanate (1451 mg, 8.2 mmol) was stirred for 48 hours, quenched with water and washed well. The organic layer was dried and filtered. It was concentrated and purified by column chromatography first eluting with 10% ethyl acetate: hexanes and then with 40% ethyl acetate: hexanes. White solid; 600 mg, 30%; MS (ESI) m / z 492.5.

실시예 96: 1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조Example 96: 1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4- Preparation of Methylpiperazin-1-yl) carbonyl] phenyl} urea

메틸 4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산 (160 mg, 0.33 mmol) 및 4-메틸피페라진으로부터 출발하여 실험 71에 요약된 절차에 따라, 표제 화합물 80 mg (44％ 수율)을 백색 고체로서 단리하였다. MS (ESI) m/z 281.2.Methyl 4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid (160 mg, 0.33 mmol) and 80 mg (44% yield) of the title compound were isolated as a white solid, following the procedure outlined in Experiment 71 starting from 4-methylpiperazine. MS (ESI) m / z 281.2.

실시예 97: 4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드의 제조Example 97: 4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N Preparation of-(1-methylpiperidin-4-yl) benzamide

메틸 4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산 (200 mg, 0.42 mmol) 및 4-아미노-1-메틸피페리딘으로부터 출발하여 실험 71에 요약된 절차에 따라, 표제 화합물 65 mg (27％ 수율)을 백색 고체로서 단리하였다. MS (ESI) m/z 574.68.Methyl 4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid (200 mg, 0.42 mmol) and 65 mg (27% yield) of the title compound were isolated as a white solid, following the procedure outlined in Experiment 71 starting from 4-amino-1-methylpiperidine. MS (ESI) m / z 574.68.

실시예 98: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(1-메틸피페리딘-4-일)우레아의 제조Example 98: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (1-methylpiperidin-4- Manufacture of urea

4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)아닐린 (140 mg 0.40 mmol) 및 4-아미노-1-메틸피페리딘 (70 mg, 0.62 mmol)으로부터 출발하여 실시예 1, 단계 3에 요약된 바와 같은 절차에 따라, 최종 화합물 20 mg (10％ 수율)을 고체로서 단리하였다. MS (ESI) m/z = 483.44- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) aniline (140 mg 0.40 mmol) and 4-amino-1-methylpiperidine (70 mg, 20 mg (10% yield) of the final compound was isolated as a solid, following the procedure as outlined in Example 1, Step 3, starting from 0.62 mmol). MS (ESI) m / z = 483.4

실시예 99: 1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(1-메틸피페리딘-4-일)우레아의 제조Example 99: 1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} Preparation of Phenyl) -3- (1-methylpiperidin-4-yl) urea

4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}아닐린 (0.140, 0.39 mmol) 및 4-아미노-1-메틸피페리딘 (70 mg, 0.62 mmol)으로부터 출발하여 실시예 81에 요약된 절차에 따라, 표제 생성물을 제조하고, HPLC로 정제하였다. 수율: 120 mg, 40％; 497.4.4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} aniline (0.140, 0.39 mmol) And starting from 4-amino-1-methylpiperidine (70 mg, 0.62 mmol) according to the procedure outlined in Example 81, the title product was prepared and purified by HPLC. Yield: 120 mg, 40%; 497.4.

실시예 100: 1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아의 제조Example 100: 1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl- [1,3,5] triazine-2- Preparation of Il] -phenyl} -3-pyridin-4-yl-urea

단계 1: 2-클로로-4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진의 제조:Step 1: Preparation of 2-chloro-4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl- [1,3,5] triazine:

질소 하에 장착된 3목 플라스크에서 2,4-디클로로-6-모르폴린-4-일-[1,3,5]트리아진 (610 mg, 2.6 mmol), 트리부틸디히드로피라닐스탄난 (1.45 g, 3.89 mmol, 1.5 eq) 및 (Ph3P)2PdCl2 (150 mg, 0.21 mmol, 0.1 eq)을 무수 디옥산 (5 ml) 중에 용해시켰다. 반응 혼합물을 16 시간 동안 교반하에 90℃로 가열하였다. 정제를 위해 실리카겔 (10 g)을 혼합물에 첨가하고, 용매를 제거하여 생성물이 실리카겔 상에 흡수되도록 하였다. 실리카겔 플러그를 컬럼 상에 놓고, 혼합물을 헥산:에틸 아세테이트 (10:1)를 사용하는 플래쉬 크로마토그래프하여, 용매 제거 후에 생성물을 회백색 고체로서 수득하였다 (345 mg = 47％ 수율); MS (ESI) m/z 281.2,4-dichloro-6-morpholin-4-yl- [1,3,5] triazine (610 mg, 2.6 mmol), tributyldihydropyranylstannan (1.45) in a three necked flask equipped with nitrogen g, 3.89 mmol, 1.5 eq) and (Ph 3 P) 2 PdCl 2 (150 mg, 0.21 mmol, 0.1 eq) were dissolved in anhydrous dioxane (5 ml). The reaction mixture was heated to 90 ° C. under stirring for 16 h. Silica gel (10 g) was added to the mixture for purification and the solvent was removed to allow the product to be absorbed onto the silica gel. The silica gel plug was placed on the column and the mixture was flash chromatographed with hexanes: ethyl acetate (10: 1) to give the product as off-white solid after solvent removal (345 mg = 47% yield); MS (ESI) m / z 281.

단계 2: 4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐아민의 제조:Step 2: 4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl- [1,3,5] triazin-2-yl] -phenyl Preparation of Amine:

마이크로파 가공 튜브에 디메톡시에탄 (4 mL), 수성 Na2CO3 (2 몰농도)(1 mL, 2 mmol, 2 eq), (Ph3P)4Pd (101 mg, 0.088 mmol), 4-아닐리노보론산 또는 에스테르 (581 mg, 2.65 mmol, 1.5 eq) 및 2-클로로-4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진 (500 mg, 1.76 mmol)을 첨가하고, 용기를 밀봉하였다. 혼합물을 60 분 동안 140℃로 가열하였다. 용매를 증류시키고, 조 화합물을 CH2Cl2/에틸 아세테이트 (10:1) 및 이후에 CH2Cl2/MeOH/NH3 (20:1:0.1)을 사용하여 실리카겔 크로마토그래피로 정제하여 생성물을 회백색 고체로서 수득하였다 (520 mg, 87％ 수율); MS (ESI) m/z 340.2Dimethoxyethane (4 mL), aqueous Na 2 CO 3 (2 molar concentrations) (1 mL, 2 mmol, 2 eq), (Ph 3 P) 4 Pd (101 mg, 0.088 mmol), 4- Anilinoboronic acid or ester (581 mg, 2.65 mmol, 1.5 eq) and 2-chloro-4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl- [ 1,3,5] triazine (500 mg, 1.76 mmol) was added and the vessel sealed. The mixture was heated to 140 ° C. for 60 minutes. The solvent was distilled off and the crude compound was purified by silica gel chromatography using CH 2 Cl 2 / ethyl acetate (10: 1) and then CH 2 Cl 2 / MeOH / NH 3 (20: 1: 0.1) to give the product. Obtained as an off-white solid (520 mg, 87% yield); MS (ESI) m / z 340.2

단계 3: 1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아의 제조:Step 3: 1- {4- [4- (3,6-Dihydro-2H-pyran-4-yl) -6-morpholin-4-yl- [1,3,5] triazin-2-yl ] -Phenyl} -3-pyridin-4-yl-urea:

CH2Cl2 (6 mL) 중 트리포스겐 (140 mg, 0.47 mmol)의 교반 용액에 4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐아민 (200 mg, 0.59 mmol)을 25℃에서 첨가하였다. 반응 혼합물을 15 분 동안 교반하고, 4-아미노피리딘 (166 mg, 1.77 mmol) 및 NEt3 (814 μL, 5.89 mmol)을 첨가하고, 반응 혼합물을 추가 1 시간 동안 교반하였다. 용매를 증류시키고, 조 혼합물을 반-정제용-HPLC (TFA-방법)로 정제하여 1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아를 수득하였다 (75 mg, 22％ 수율); MS (ESI) m/z 460To a stirred solution of triphosgen (140 mg, 0.47 mmol) in CH 2 Cl 2 (6 mL) 4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholine-4 -Yl- [1,3,5] triazin-2-yl] -phenylamine (200 mg, 0.59 mmol) was added at 25 ° C. The reaction mixture was stirred for 15 minutes, 4-aminopyridine (166 mg, 1.77 mmol) and NEt 3 (814 μL, 5.89 mmol) were added and the reaction mixture was stirred for an additional 1 hour. The solvent was distilled off and the crude mixture was purified by semi-prep-HPLC (TFA-method) to give 1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-mor Polin-4-yl- [1,3,5] triazin-2-yl] -phenyl} -3-pyridin-4-yl-urea was obtained (75 mg, 22% yield); MS (ESI) m / z 460

실시예 101: 1-{4-[4-모르폴린-4-일-6-(테트라히드로-피란-4-일)-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아의 제조Example 101: 1- {4- [4-Morpholin-4-yl-6- (tetrahydro-pyran-4-yl)-[1,3,5] triazin-2-yl] -phenyl}- Preparation of 3-pyridin-4-yl-urea

1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아 (130 mg, 0.28 mmol) 및 Pd-C (10％, 습윤) (113 mg)를 메탄올/THF/CH2Cl2 (4:1:1) (30 mL) 중에 현탁시키고, 3 시간 동안 수소화시켰다 (1 기압). 완료 후에, 촉매를 셀라이트™ 상에서 여과에 의해 제거하고, 용매를 진공하에 제거하여 조 생성물을 수득하고, 이것을 반-정제용-HPLC (TFA-방법)로 정제하여, 1-{4-[4-모르폴린-4-일-6-(테트라히드로-피란-4-일)-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아를 수득하였다 (32 mg = 20％ 수율); MS (ESI) m/z 462.1- {4- [4- (3,6-Dihydro-2H-pyran-4-yl) -6-morpholin-4-yl- [1,3,5] triazin-2-yl] -phenyl } -3-pyridin-4-yl-urea (130 mg, 0.28 mmol) and Pd-C (10%, wet) (113 mg) were added to methanol / THF / CH 2 Cl 2 (4: 1: 1) (30 mL) and hydrogenated for 3 h (1 atm). After completion, the catalyst was removed by filtration on Celite ™ and the solvent was removed in vacuo to afford the crude product, which was purified by semi-prep-HPLC (TFA-method) to give 1- {4- [4 Obtain morpholin-4-yl-6- (tetrahydro-pyran-4-yl)-[1,3,5] triazin-2-yl] -phenyl} -3-pyridin-4-yl-urea (32 mg = 20% yield); MS (ESI) m / z 462.

실시예 102: 1-{4-[4-(8-메틸-8-아자-비시클로[3.2.1]옥트-3-일옥시)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아의 제조Example 102: 1- {4- [4- (8-methyl-8-aza-bicyclo [3.2.1] oct-3-yloxy) -6-morpholin-4-yl- [1,3, 5] Triazin-2-yl] -phenyl} -3-pyridin-4-yl-urea

단계 1: 3-(4-클로로-6-모르폴린-4-일-[1,3,5]트리아진-2-일옥시)-8-메틸-8-아자-비시클로[3.2.1]옥탄의 제조:Step 1: 3- (4-Chloro-6-morpholin-4-yl- [1,3,5] triazin-2-yloxy) -8-methyl-8-aza-bicyclo [3.2.1] Preparation of Octane:

교반 막대가 장착된 3목 플라스크에서 N2 분위기 하에 트로핀 (1 g, 4.24 mmol)을 (무수) THF (15 mL) 중에 현탁시켰다. 혼합물을 -78℃로 냉각시키고, BuLi (THF 중 2M) (5.53 ml, 1.2 eq)를 적가하고, 혼합물을 30 분에 걸쳐 25℃로 가온시켰다. 반응 혼합물에 2,4-디클로로-6-모르폴린-4-일-[1,3,5]트리아진 (996 mg, 4,24, mmole)을 첨가하고, 밤새 교반되도록 하였다. 후처리를 위해, 에테르 (100 mL)를 첨가하였다. 유기층을 물 (20 mL) 및 염수 (20 mL)로 세척하고, MgSO4 상에서 건조시켰다. 여과하고 용매를 제거하여 무색 오일을 수득하였다. CH2Cl2/MeOH/NH3 (15:1:0.1)을 사용하는 플래쉬-크로마토그래피로 더 정제하여 생성물을 백색 고체로서 수득하였다 (600 mg, 42％ 수율); MS (ESI) m/z 340Troffin (1 g, 4.24 mmol) was suspended in (anhydrous) THF (15 mL) in an N 2 atmosphere in a three neck flask equipped with a stir bar. The mixture was cooled to -78 ° C, BuLi (2M in THF) (5.53 ml, 1.2 eq) was added dropwise and the mixture was warmed to 25 ° C over 30 minutes. 2,4-Dichloro-6-morpholin-4-yl- [1,3,5] triazine (996 mg, 4,24, mmole) was added to the reaction mixture and allowed to stir overnight. For workup, ether (100 mL) was added. The organic layer was washed with water (20 mL) and brine (20 mL) and dried over MgSO 4 . Filtration and removal of solvent gave a colorless oil. Further purification by flash-chromatography with CH 2 Cl 2 / MeOH / NH 3 (15: 1: 0.1) gave the product as a white solid (600 mg, 42% yield); MS (ESI) m / z 340

단계 2: 4-[4-(8-메틸-8-아자-비시클로[3.2.1]옥트-3-일옥시)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐아민의 제조:Step 2: 4- [4- (8-methyl-8-aza-bicyclo [3.2.1] oct-3-yloxy) -6-morpholin-4-yl- [1,3,5] triazine 2-yl] -phenylamine:

마이크로파 가공 튜브에 디메톡시에탄 (4 mL), 수성 Na2CO3 (2 몰)(1 mL, 2 mmol, 2 eq), (Ph3P)4Pd (85 mg, 0.074 mmol), 4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보롤란-2-일)-페닐아민 (482 mg, 2.21 mmol, 1.5 eq) 및 3-(4-클로로-6-모르폴린-4-일-[1,3,5]트리아진-2-일옥시)-8-메틸-8-아자-비시클로[3.2.1]옥탄 (500 mg, 1.47 mmol)을 첨가하고, 용기를 밀봉하였다. 혼합물을 60 분 동안 140℃로 가열하였다. 용매를 증류시키고, 조 화합물을 CH2Cl2/에틸 아세테이트 (10:1) 및 이후에 CH2Cl2/MeOH/NH3 (10:1:0.1)을 사용하는 실리카겔 크로마토그래피로 정제하여 생성물을 회백색 고체로서 수득하였다 (300 mg, 51％ 수율); MS (ESI) m/z 369.Dimethoxyethane (4 mL), aqueous Na 2 CO 3 (2 mol) (1 mL, 2 mmol, 2 eq), (Ph 3 P) 4 Pd (85 mg, 0.074 mmol), 4- ( 4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -phenylamine (482 mg, 2.21 mmol, 1.5 eq) and 3- (4-chloro-6- Morpholin-4-yl- [1,3,5] triazin-2-yloxy) -8-methyl-8-aza-bicyclo [3.2.1] octane (500 mg, 1.47 mmol) was added, The container was sealed. The mixture was heated to 140 ° C. for 60 minutes. The solvent was distilled off and the crude compound was purified by silica gel chromatography using CH 2 Cl 2 / ethyl acetate (10: 1) followed by CH 2 Cl 2 / MeOH / NH 3 (10: 1: 0.1). Obtained as an off-white solid (300 mg, 51% yield); MS (ESI) m / z 369.

단계 3: 1-{4-[4-(8-메틸-8-아자-비시클로[3.2.1]옥트-3-일옥시)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아의 제조:Step 3: 1- {4- [4- (8-Methyl-8-aza-bicyclo [3.2.1] oct-3-yloxy) -6-morpholin-4-yl- [1,3,5 ] Triazin-2-yl] -phenyl} -3-pyridin-4-yl-urea:

CH2Cl2 (3 mL) 중 트리포스겐 (60 mg, 0.20 mmol)의 교반 용액에 4-[4-(8-메틸-8-아자-비시클로[3.2.1]옥트-3-일옥시)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐아민 (100 mg, 0.25 mmol)을 25℃에서 첨가하였다. 반응 혼합물을 15 분 동안 교반하고, 4-아미노피리딘 (70 mg, 0.75 mmol) 및 NEt3 (346 μL, 2.5 mmol)을 첨가하고, 반응 혼합물을 추가 1 시간 동안 교반하였다. 용매를 제거하고, 조 혼합물을 반-정제용-HPLC (NH3-방법)로 정제하여 1-{4-[4-(8-메틸-8-아자-비시클로[3.2.1]옥트-3-일옥시)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아를 수득하였다 (28 mg, 22％ 수율); MS (ESI)m/z 517.To a stirred solution of triphosgen (60 mg, 0.20 mmol) in CH 2 Cl 2 (3 mL) 4- [4- (8-methyl-8-aza-bicyclo [3.2.1] oct-3-yloxy) -6-Morpholin-4-yl- [1,3,5] triazin-2-yl] -phenylamine (100 mg, 0.25 mmol) was added at 25 ° C. The reaction mixture was stirred for 15 minutes, 4-aminopyridine (70 mg, 0.75 mmol) and NEt 3 (346 μL, 2.5 mmol) were added and the reaction mixture was stirred for an additional 1 hour. The solvent was removed and the crude mixture was purified by semi-prep-HPLC (NH 3 -method) to give 1- {4- [4- (8-methyl-8-aza-bicyclo [3.2.1] oct-3 -Yloxy) -6-morpholin-4-yl- [1,3,5] triazin-2-yl] -phenyl} -3-pyridin-4-yl-urea was obtained (28 mg, 22% yield); MS (ESI) m / z 517.

실시예 103: 4-(3-{4-[4-(8-메틸-8-아자-비시클로[3.2.1]옥트-3-일옥시)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-우레이도)-벤즈아미드의 제조Example 103: 4- (3- {4- [4- (8-methyl-8-aza-bicyclo [3.2.1] oct-3-yloxy) -6-morpholin-4-yl- [1 , 3,5] triazin-2-yl] -phenyl} -ureido) -benzamide

CH2Cl2 (3 mL) 중 트리포스겐 (120 mg, 0.40 mmol)의 교반 용액에 4-[4-(8-메틸-8-아자-비시클로[3.2.1]옥트-3-일옥시)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐아민 (200 mg, 0.5 mmol)를 25℃에서 첨가하였다. 반응 혼합물을 15 분 동안 교반하고, 4-아미노벤즈아미드 (204 mg, 1.5 mmol) 및 NEt3 (692 μL, 5 mmol)을 첨가하고, 반응 혼합물을 추가 1 시간 동안 교반하였다. 용매를 제거하고, 조 혼합물을 반-정제용-HPLC (NH3-방법)로 정제하여 4-(3-{4-[4-(8-메틸-8-아자-비시클로[3.2.1]옥트-3-일옥시)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-우레이도)-벤즈아미드를 수득하였다 (42 mg, 15％ 수율). MS (ESI) m/z 559.To a stirred solution of triphosgen (120 mg, 0.40 mmol) in CH 2 Cl 2 (3 mL) 4- [4- (8-methyl-8-aza-bicyclo [3.2.1] oct-3-yloxy) -6-Morpholin-4-yl- [1,3,5] triazin-2-yl] -phenylamine (200 mg, 0.5 mmol) was added at 25 ° C. The reaction mixture was stirred for 15 minutes, 4-aminobenzamide (204 mg, 1.5 mmol) and NEt 3 (692 μL, 5 mmol) were added and the reaction mixture was stirred for an additional 1 hour. The solvent was removed and the crude mixture was purified by semi-prep-HPLC (NH 3 -method) to give 4- (3- {4- [4- (8-methyl-8-aza-bicyclo [3.2.1] Octoc-3-yloxy) -6-morpholin-4-yl- [1,3,5] triazin-2-yl] -phenyl} -ureido) -benzamide was obtained (42 mg, 15% yield). MS (ESI) m / z 559.

실시예 104: 3-({4-모르폴린-4-일-6-[4-(3-피리딘-4-일-우레이도)-페닐]-[1,3,5]트리아진-2-일아미노}-메틸)-아제티딘-1-카르복실산 tert-부틸 에스테르의 제조Example 104: 3-({4-morpholin-4-yl-6- [4- (3-pyridin-4-yl-ureido) -phenyl]-[1,3,5] triazine-2- Preparation of monoamino} -methyl) -azetidine-1-carboxylic acid tert-butyl ester

단계 1: 3-[(4-클로로-6-모르폴린-4-일-[1,3,5]트리아진-2-일아미노)-메틸]-아제티딘-1-카르복실산 tert-부틸 에스테르의 제조:Step 1: 3-[(4-chloro-6-morpholin-4-yl- [1,3,5] triazin-2-ylamino) -methyl] -azetidine-1-carboxylic acid tert-butyl Preparation of esters:

THF (10 mL) 중 3-아미노메틸-아제티딘-1-카르복실산 tert-부틸 에스테르 HCl 염 (945 mg, 4.24 mmol) 및 NEt3 (856 mg, 8.48 mmol)의 용액에 0℃에서 2,4-디클로로-6-모르폴린-4-일-[1,3,5]트리아진 (996 mg, 4.24 mmol)의 현탁액을 0℃에서 첨가하였다. 반응 혼합물을 또다른 1 시간 동안 0℃에서 교반하고, 20℃로 가온되도록 하고, 1 내지 4 시간 동안 교반하여 반응이 완결되도록 추진하였다. 실리카겔 (20 g)을 반응 혼합물에 첨가하고, 용매를 제거하여 생성물을 실리카겔 상에 흡수시켰다. 실리카겔 플러그를 컬럼 최상부에 놓아 CH2Cl2/MeOH/NH3 (20:1:01) 용리액을 사용하는 플래쉬 크로마토그래피로 정제하였다. 생성물 분획을 통합하고 용매를 증발시킨 후에, 생성물 (750 mg, 46％ 수율)을 황색 고체로서 수득하였다; MS (ESI) m/z 385To a solution of 3-aminomethyl-azetidine-1-carboxylic acid tert-butyl ester HCl salt (945 mg, 4.24 mmol) and NEt 3 (856 mg, 8.48 mmol) in THF (10 mL) at 2 ° C. A suspension of 4-dichloro-6-morpholin-4-yl- [1,3,5] triazine (996 mg, 4.24 mmol) was added at 0 ° C. The reaction mixture was stirred at 0 ° C. for another 1 hour, allowed to warm to 20 ° C. and stirred for 1-4 hours to drive the reaction to completion. Silica gel (20 g) was added to the reaction mixture and the solvent was removed to absorb the product on silica gel. The silica gel plug was placed on top of the column and purified by flash chromatography using CH 2 Cl 2 / MeOH / NH 3 (20: 1: 01) eluent. After integrating the product fractions and evaporating the solvent, the product (750 mg, 46% yield) was obtained as a yellow solid; MS (ESI) m / z 385

단계 2: 3-{[4-(4-아미노-페닐)-6-모르폴린-4-일-[1,3,5]트리아진-2-일아미노]-메틸}-아제티딘-1-카르복실산 tert-부틸 에스테르의 제조:Step 2: 3-{[4- (4-amino-phenyl) -6-morpholin-4-yl- [1,3,5] triazin-2-ylamino] -methyl} -azetidine-1- Preparation of carboxylic acid tert-butyl esters:

마이크로파 가공 튜브에 디메톡시에탄 (15 mL), 수성 Na2CO3 (2 몰농도)(4 mL, 8 mmol, 2 eq), (Ph3P)4Pd (317 mg, 0.55 mmol), 4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보롤란-2-일)-페닐아민 (1.81 g, 8.30 mmol, 1.5 eq) 및 3-[(4-클로로-6-모르폴린-4-일-[1,3,5]트리아진-2-일아미노)-메틸]-아제티딘-1-카르복실산 tert-부틸 에스테르 (1.3 g, 5.53 mmol)를 첨가하고, 용기를 밀봉하였다. 혼합물을 60 분 동안 140℃로 가열하였다. 용매를 제거하고, 조 화합물을 CH2Cl2/에틸 아세테이트 (10:1) 및 이후에 CH2Cl2/MeOH/NH3 (15:1:0.1)을 사용하는 실리카겔 크로마토그래피로 정제하여 생성물을 회백색 고체로서 수득하였다 (1.3 g, 53％ 수율).Dimethoxyethane (15 mL), aqueous Na 2 CO 3 (2 molar concentrations) (4 mL, 8 mmol, 2 eq), (Ph 3 P) 4 Pd (317 mg, 0.55 mmol), 4- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -phenylamine (1.81 g, 8.30 mmol, 1.5 eq) and 3-[(4-chloro- 6-Morpholin-4-yl- [1,3,5] triazin-2-ylamino) -methyl] -azetidine-1-carboxylic acid tert-butyl ester (1.3 g, 5.53 mmol) was added The container was sealed. The mixture was heated to 140 ° C. for 60 minutes. The solvent was removed and the crude compound was purified by silica gel chromatography using CH 2 Cl 2 / ethyl acetate (10: 1) followed by CH 2 Cl 2 / MeOH / NH 3 (15: 1: 0.1) to give the product. Obtained as an off-white solid (1.3 g, 53% yield).

MS (ESI) m/z = 442MS (ESI) m / z = 442

단계 3: 3-({4-모르폴린-4-일-6-[4-(3-피리딘-4-일-우레이도)-페닐]-[1,3,5]트리아진-2-일아미노}-메틸)-아제티딘-1-카르복실산 tert-부틸 에스테르의 제조Step 3: 3-({4-morpholin-4-yl-6- [4- (3-pyridin-4-yl-ureido) -phenyl]-[1,3,5] triazin-2-yl Preparation of amino} -methyl) -azetidine-1-carboxylic acid tert-butyl ester

CH2Cl2 (5 mL) 중 트리포스겐 (269 mg, 0.90 mmol)의 교반 용액에 3-{[4-(4-아미노-페닐)-6-모르폴린-4-일-[1,3,5]트리아진-2-일아미노]-메틸}-아제티딘-1-카르복실산 tert-부틸 에스테르 (500 mg, 1.13 mmol)를 25℃에서 첨가하였다. 반응 혼합물을 15 분 동안 교반하고, 4-아미노피리딘 (319 mg, 3.39 mmol) 및 NEt3 (1.56 mL, 11.3 mmol)을 첨가하고, 반응 혼합물을 추가 1 시간 동안 교반하였다. 용매를 회전 증발기 상에서 제거하고, 조 혼합물을 반-정제용-HPLC (TFA-방법)로 정제하여 3-({4-모르폴린-4-일-6-[4-(3-피리딘-4-일-우레이도)-페닐]-[1,3,5]트리아진-2-일아미노}-메틸)-아제티딘-1-카르복실산 tert-부틸 에스테르를 수득하였다 (150 mg, 16％ 수율); MS (ESI) m/z 562.To a stirred solution of triphosgen (269 mg, 0.90 mmol) in CH 2 Cl 2 (5 mL) 3-{[4- (4-amino-phenyl) -6-morpholin-4-yl- [1,3, 5] triazin-2-ylamino] -methyl} -azetidine-1-carboxylic acid tert-butyl ester (500 mg, 1.13 mmol) was added at 25 ° C. The reaction mixture was stirred for 15 minutes, 4-aminopyridine (319 mg, 3.39 mmol) and NEt 3 (1.56 mL, 11.3 mmol) were added and the reaction mixture was stirred for an additional 1 hour. The solvent is removed on a rotary evaporator and the crude mixture is purified by semi-prep-HPLC (TFA-method) to give 3-({4-morpholin-4-yl-6- [4- (3-pyridine-4- Il-ureido) -phenyl]-[1,3,5] triazin-2-ylamino} -methyl) -azetidine-1-carboxylic acid tert-butyl ester was obtained (150 mg, 16% yield) ); MS (ESI) m / z 562.

실시예 105: 1-(4-{4-[(아제티딘-3-일메틸)-아미노]-6-모르폴린-4-일-[1,3,5]트리아진-2-일}-페닐)-3-피리딘-4-일-우레아의 제조Example 105: 1- (4- {4-[(azetidin-3-ylmethyl) -amino] -6-morpholin-4-yl- [1,3,5] triazin-2-yl}- Preparation of Phenyl) -3-pyridin-4-yl-urea

3-({4-모르폴린-4-일-6-[4-(3-피리딘-4-일-우레이도)-페닐]-[1,3,5]트리아진-2-일아미노}-메틸)-아제티딘-1-카르복실산 tert-부틸 에스테르 (100 mg, 0.18 mmol)를 CH2Cl2 (1 mL) 중에 용해시키고, TFA (1 mL)를 첨가하였다. 이것을 16 시간 동안 25℃에서 교반한 다음, 용매를 감압하에 제거하고, 잔류물을 아세토니트릴/MeOH (1:1) (2 mL)로 처리하여 백색 고체를 수득하고, 이것을 여과에 의해 수집하여 생성물을 비스-TFA 염으로서 수득하였다 (59 mg, 46％ 수율). MS(ESI) m/z 462.3-({4-morpholin-4-yl-6- [4- (3-pyridin-4-yl-ureido) -phenyl]-[1,3,5] triazin-2-ylamino}- Methyl) -azetidine-1-carboxylic acid tert-butyl ester (100 mg, 0.18 mmol) was dissolved in CH 2 Cl 2 (1 mL) and TFA (1 mL) was added. It is stirred at 25 ° C. for 16 h, then the solvent is removed under reduced pressure and the residue is treated with acetonitrile / MeOH (1: 1) (2 mL) to give a white solid which is collected by filtration to give the product Was obtained as the bis-TFA salt (59 mg, 46% yield). MS (ESI) m / z 462.

실시예 106: Tert-부틸 4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트의 제조Example 106 Tert-Butyl 4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (3-pyridin-4-ylureido) phenyl ) -1,3,5-triazin-2-yl) piperazine-1-carboxylate

Tert-부틸 4-(4,6-디클로로-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트를 문헌 [Loewik, D.W.P.M. and Lowe, C.R. Eur. J. Org. Chem. 2001, 2825-2839]에 따라 제조하였다.Tert-butyl 4- (4,6-dichloro-1,3,5-triazin-2-yl) piperazine-1-carboxylate is described in Loewik, D.W.P.M. and Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839.

단계 1: tert-부틸 4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트의 제조:Step 1: tert-butyl 4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro-1,3,5-triazin-2-yl) pipe Preparation of Razine-1-carboxylate:

물 (18 mL) 중 8-옥사-3-아자비시클로[3.2.1]옥탄 히드로클로라이드 (0.49 g, 3.3 mmol)의 용액에 아세톤 (약 10 mL) 중 tert-부틸 4-(4,6-디클로로-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트 (1.0 g, 3.0 mmol)의 현탁액을 첨가하였다. 현탁액을 자기 교반하면서, 고체 탄산나트륨 (0.70 g, 6.6 mmol)을 단일 부분으로 첨가하였다. 혼합물을 2 시간 동안 교반하면서, 오일조 내 70 내지 75℃에서 가열하였다. 혼합물이 실온으로 냉각되도록 한 후에, 표제 화합물을 여과에 의해 제거하고, 물로 세척하고, 진공하에 건조시켰다.To a solution of 8-oxa-3-azabicyclo [3.2.1] octane hydrochloride (0.49 g, 3.3 mmol) in water (18 mL) tert-butyl 4- (4,6-dichloro in acetone (about 10 mL) A suspension of -1,3,5-triazin-2-yl) piperazine-1-carboxylate (1.0 g, 3.0 mmol) was added. While stirring the suspension, solid sodium carbonate (0.70 g, 6.6 mmol) was added in a single portion. The mixture was heated at 70-75 ° C. in an oil bath with stirring for 2 hours. After allowing the mixture to cool to room temperature, the title compound was removed by filtration, washed with water and dried in vacuo.

MS (ES+) 411.0, 412.3 (M+H)+MS (ES +) 411.0, 412.3 (M + H) &lt; + &gt;

단계 2: tert-부틸 4-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트의 제조:Step 2: tert-Butyl 4- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -1,3,5-triazine- Preparation of 2-yl) piperazine-1-carboxylate:

수성 2 M 탄산나트륨 용액 (3 mL) 및 1:1 에탄올/톨루엔 (12 mL) 중 tert-부틸 4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트 (1.0 g, 2.4 mmol), 4-아미노페닐보론산, 피나콜 에스테르 (0.69 g, 3.2 mmol) 및 테트라키스(트리페닐포스핀)팔라듐 (0.28 g, 0.24 mmol)의 현탁액을 120℃에서 1 시간 동안 마이크로파에서 조사시켰다. 냉각시킨 후, 2상 혼합물을 에틸 아세테이트로 3회 추출하였다. 추출물을 포화 수성 염화나트륨 용액으로 세척하고, 무수 황산마그네슘 상에서 건조시키고, 여과하고, 감압하에 농축 건조시켜 표제 화합물을 수득하였다.Tert-butyl 4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl)-in aqueous 2 M sodium carbonate solution (3 mL) and 1: 1 ethanol / toluene (12 mL)- 6-chloro-1,3,5-triazin-2-yl) piperazin-1-carboxylate (1.0 g, 2.4 mmol), 4-aminophenylboronic acid, pinacol esters (0.69 g, 3.2 mmol) And a suspension of tetrakis (triphenylphosphine) palladium (0.28 g, 0.24 mmol) in microwave at 120 ° C. for 1 hour. After cooling, the biphasic mixture was extracted three times with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure to afford the title compound.

MS (ES+) 468.1 (M+H)+MS (ES +) 468.1 (M + H) &lt; + &gt;

단계 3: tert-부틸 4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트의 제조:Step 3: tert-butyl 4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (3-pyridin-4-ylureido) phenyl) Preparation of -1,3,5-triazin-2-yl) piperazine-1-carboxylate:

조 tert-부틸 4-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트 (대략 1.4 mmol)를 테트라히드로푸란 (20 mL) 중에 용해시킨 후에, 트리포스겐 (0.30 g, 1.0 mmol) 및 트리에틸아민 (2 mL)으로 순서대로 처리하였다. 5 분 후에, 혼합물을 테트라히드로푸란 중 4-아미노피리딘 (0.53 g, 5.6 mmol)의 용액으로 처리하였다. 혼합물을 감압하에 농축시켜 조 tert-부틸 4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트를 수득하고, 이의 샘플을 역상 HPLC로 정제하여 순수한 표제 화합물을 수득하였다.Crude tert-butyl 4- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -1,3,5-triazine-2- I) piperazine-1-carboxylate (approximately 1.4 mmol) was dissolved in tetrahydrofuran (20 mL) and then treated sequentially with triphosgen (0.30 g, 1.0 mmol) and triethylamine (2 mL). . After 5 minutes, the mixture was treated with a solution of 4-aminopyridine (0.53 g, 5.6 mmol) in tetrahydrofuran. The mixture was concentrated under reduced pressure to afford crude tert-butyl 4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (3-pyridin-4-ylurei). Phenyl) -1,3,5-triazin-2-yl) piperazin-1-carboxylate was obtained and the samples thereof were purified by reverse phase HPLC to give the pure title compound.

MS (ES+) 588.2 (M+H)+MS (ES +) 588.2 (M + H) &lt; + &gt;

실시예 107: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페라진-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조Example 107: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (piperazin-1-yl) -1,3,5- Preparation of Triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea

조 tert-부틸 4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)피페라진-1-카르복실레이트 (대략 1.4 mmol)를 디클로로메탄 (20 mL) 중에 녹이고, 트리플루오로아세트산 (5 mL)으로 처리하였다. 혼합물을 감압하에 농축시켰다. 잔류물에 디에틸 에테르를 첨가하여 표제 화합물을 고체 디-TFA 염으로서 수득하고, 이것을 여과에 의해 수집하고, 하우스 진공하에 건조시켰다; MS (ES+) 488.1 (M+H)+Crude tert-butyl 4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (3-pyridin-4-ylureido) phenyl) -1 , 3,5-triazin-2-yl) piperazine-1-carboxylate (approximately 1.4 mmol) was dissolved in dichloromethane (20 mL) and treated with trifluoroacetic acid (5 mL). The mixture was concentrated under reduced pressure. Diethyl ether was added to the residue to give the title compound as a solid di-TFA salt, which was collected by filtration and dried under house vacuum; MS (ES +) 488.1 (M + H) &lt; + &gt;

실시예 108: 1-{4-[4-(4-메틸피페라진-1-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 108: 1- {4- [4- (4-methylpiperazin-1-yl) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3 Preparation of, 5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea

1:1 98％ 포름산 및 37％ 포르말린 (4 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페라진-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·2TFA (115 mg)를 75℃에서 90 분 동안 가열한 후에, 농축시켜 건조시키고, HPLC 상에서 정제하여 표제 화합물을 그의 디-TFA 염으로서 수득하였다; MS (ES+) 502.3 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (piperazin-) in 1: 1 98% formic acid and 37% formalin (4 mL) 1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea.2TFA (115 mg) was heated at 75 ° C. for 90 minutes, then concentrated Dried and purified on HPLC to afford the title compound as its di-TFA salt; MS (ES +) 502.3 (M + H) +

실시예 109: 1-{4-[4-(4-벤질피페라진-1-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 109: 1- {4- [4- (4-benzylpiperazin-1-yl) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3 Preparation of, 5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea

디클로로메탄 (4 mL) 및 트리에틸아민 (0.10 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페라진-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·2TFA (130 mg)를 벤즈알데히드 (0.10 mL)에 이어 나트륨 트리아세톡시보로히드라이드 (80 mg)로 처리하였다. 혼합물을 농축시켜 건조시키고, HPLC 상에서 정제하여 표제 화합물을 그의 디-TFA 염으로서 수득하였다; MS (ES+) 578.3 (M+H)+.1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (piperazin-) in dichloromethane (4 mL) and triethylamine (0.10 mL) 1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea.2TFA (130 mg) followed by benzaldehyde (0.10 mL) followed by sodium triacetoxyboro Treated with hydride (80 mg). The mixture was concentrated to dryness and purified on HPLC to afford the title compound as its di-TFA salt; MS (ES +) 578.3 (M + H) &lt; + &gt;.

실시예 110: 1-(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[4-(피리딘-3-일메틸)피페라진-1-일]-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 110: 1- (4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- [4- (pyridin-3-ylmethyl) piperazin-1 Preparation of -yl] -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea

디클로로메탄 (4 mL) 및 트리에틸아민 (0.12 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페라진-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·2TFA (150 mg)를 3-피리딘카르복스알데히드 (0.1 mL)에 이어 나트륨 트리아세톡시보로히드라이드 (80 mg)로 처리하였다. 혼합물을 농축시켜 건조시키고, HPLC 상에서 정제하여 표제 화합물을 그의 트리-TFA 염으로서 수득하였다; MS (ES+) 579.3 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (piperazine-) in dichloromethane (4 mL) and triethylamine (0.12 mL) 1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea.2TFA (150 mg) followed by 3-pyridinecarboxaldehyde (0.1 mL) Treated with sodium triacetoxyborohydride (80 mg). The mixture was concentrated to dryness and purified on HPLC to afford the title compound as its tri-TFA salt; MS (ES +) 579.3 (M + H) &lt; + &gt;

실시예 111: 1-{4-[4-(4-아세틸피페라진-1-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 111: 1- {4- [4- (4-acetylpiperazin-1-yl) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3 Preparation of, 5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea

디클로로메탄 (4 mL) 및 트리에틸아민 (1 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페라진-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·2TFA (230 mg)를 아세틸 클로라이드로 처리하였다. 혼합물을 농축시켜 건조시키고, HPLC 상에서 정제하여 표제 화합물을 그의 TFA 염으로서 수득하였다; MS (ES+) 530.3 (M+H)+.1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (piperazine-) in dichloromethane (4 mL) and triethylamine (1 mL) 1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea.2TFA (230 mg) was treated with acetyl chloride. The mixture was concentrated to dryness and purified on HPLC to afford the title compound as its TFA salt; MS (ES +) 530.3 (M + H) &lt; + &gt;.

실시예 112: 1-(4-{4-[4-(N,N-디메틸글리실)피페라진-1-일]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 112: 1- (4- {4- [4- (N, N-dimethylglycyl) piperazin-1-yl] -6- (8-oxa-3-azabicyclo [3.2.1] oct- Preparation of 3-yl) -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea

디클로로메탄 (4 mL) 및 트리에틸아민 (1 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페라진-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·2TFA (64 mg)를 디메틸아미노아세틸 클로라이드 히드로클로라이드 (100 mg)로 처리하였다. 혼합물을 힛건으로 가열한 후에, 농축시켜 건조시키고, HPLC 상에서 정제하여 표제 화합물을 그의 디-TFA 염으로서 수득하였다; MS (ES+) 573.3 (M+H)+.1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (piperazine-) in dichloromethane (4 mL) and triethylamine (1 mL) Treatment of 1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea.2TFA (64 mg) with dimethylaminoacetyl chloride hydrochloride (100 mg) It was. The mixture was heated with heat, concentrated to dryness and purified on HPLC to afford the title compound as its di-TFA salt; MS (ES +) 573.3 (M + H) &lt; + &gt;.

실시예 113: 1-{4-[4-(4-이소니코티노일피페라진-1-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 113: 1- {4- [4- (4-isonicotinoylpiperazin-1-yl) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl)- Preparation of 1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea

디클로로메탄 (4 mL) 및 트리에틸아민 (1 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페라진-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·2TFA (100 mg)를 이소니코티노일 클로라이드 (100 mg)로 처리하였다. 혼합물을 농축시켜 건조시키고, HPLC 상에서 정제하여 표제 화합물을 그의 디-TFA 염으로서 수득하였다; MS (ES+) 593.1 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (piperazine-) in dichloromethane (4 mL) and triethylamine (1 mL) 1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea.2TFA (100 mg) was treated with isicotinoyl chloride (100 mg). . The mixture was concentrated to dryness and purified on HPLC to afford the title compound as its di-TFA salt; MS (ES +) 593.1 (M + H) &lt; + &gt;

실시예 114: 메틸 4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]피페라진-1-카르복실레이트의 제조Example 114 Methyl 4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl } -1,3,5-triazin-2-yl] piperazine-1-carboxylate

디클로로메탄 (2 mL), 테트라히드로푸란 (2 mL) 및 트리에틸아민 (1 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(피페라진-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·2TFA (75 mg)를 메틸 클로로포르메이트 (0.10 mL)로 처리하였다. 혼합물을 농축시켜 건조시키고, RP-HPLC 상에서 정제하여 표제 화합물을 그의 TFA 염으로서 수득하였다. MS (ES+) 546.3 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) in dichloromethane (2 mL), tetrahydrofuran (2 mL) and triethylamine (1 mL) ) -6- (piperazin-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea · 2TFA (75 mg) to methyl chloroformate (0.10 mL). The mixture was concentrated to dryness and purified on RP-HPLC to afford the title compound as its TFA salt. MS (ES +) 546.3 (M + H) &lt; + &gt;

실시예 115: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조Example 115: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea

단계 1: 1-(4,6-디클로로-1,3,5-트리아진-2-일)피페리딘-4-온의 제조:Step 1: Preparation of 1- (4,6-dichloro-1,3,5-triazin-2-yl) piperidin-4-one:

자기 교반된 빙수 (72 mL)에 아세톤 (48 mL) 중 시아누르산 클로라이드 (2.2 g, 12 mmol)의 용액을 첨가한 다음, 피페리돈 일수화물 히드로클로라이드 (1.8 g, 12 mmol)를 아세톤 (20 mL) 및 물 (10 mL) 중의 현탁액으로서 첨가하였다. 혼합물에 물 (25 mL) 중 탄산수소나트륨 (2.2 g, 24 mmol)의 현탁액을 첨가하였다. 혼합물을 0℃에서 2 시간 동안 교반하였다. 표제 화합물을 여과에 의해 수집하고, 물로 세척하고, 진공하에 건조시켰다.To a magnetically stirred ice water (72 mL) was added a solution of cyanuric chloride (2.2 g, 12 mmol) in acetone (48 mL), followed by piperidon monohydrate hydrochloride (1.8 g, 12 mmol) to acetone (20 mL) and water (10 mL) as a suspension. To the mixture was added a suspension of sodium hydrogen carbonate (2.2 g, 24 mmol) in water (25 mL). The mixture was stirred at 0 ° C for 2 h. The title compound was collected by filtration, washed with water and dried in vacuo.

MS (ES+) 248.8 (M+H)+MS (ES +) 248.8 (M + H) &lt; + &gt;

단계 2: 1-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-1,3,5-트리아진-2-일)피페리딘-4-온의 제조:Step 2: 1- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro-1,3,5-triazin-2-yl) piperidine- Preparation of 4-ones:

8-옥사-3-아자비시클로[3.2.1]옥탄 히드로클로라이드 (66 mL)의 수용액에 1-(4,6-디클로로-1,3,5-트리아진-2-일)피페리딘-4-온 (2.7 g, 11 mmol)을 아세톤 (40 mL) 중의 현탁액으로서 첨가하였다. 혼합물에 고체 탄산나트륨 (2.5 g, 24 mmol)을 첨가하였다. 현탁액을 80℃에서 2 시간 동안 교반한 후에, 실온으로 냉각시켰다. 표제 화합물을 여과에 의해 수집하고, 물로 세척하고, 진공하에 건조시켰다; MS (ES+) 324.4 (M+H)+1- (4,6-dichloro-1,3,5-triazin-2-yl) piperidine-4 in an aqueous solution of 8-oxa-3-azabicyclo [3.2.1] octane hydrochloride (66 mL) -One (2.7 g, 11 mmol) was added as a suspension in acetone (40 mL). To the mixture was added solid sodium carbonate (2.5 g, 24 mmol). The suspension was stirred at 80 ° C. for 2 hours and then cooled to room temperature. The title compound was collected by filtration, washed with water and dried in vacuo; MS (ES +) 324.4 (M + H) &lt; + &gt;

단계 3: 1-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일)피페리딘-4-온의 제조:Step 3: 1- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -1,3,5-triazin-2-yl Preparation of Piperidin-4-one:

수성 2 M 탄산나트륨 용액 (3 mL) 및 1:1 에탄올/톨루엔 (12 mL) 중 1-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-1,3,5-트리아진-2-일)피페리딘-4-온 (1.0 g, 3.1 mmol), 4-아미노페닐보론산, 피나콜 에스테르 (1.0 g, 4.7 mmol) 및 테트라키스(트리페닐포스핀)팔라듐 (0.20 g, 0.17 mmol)의 현탁액을 120℃에서 1 시간 동안 마이크로파로 조사시켰다. 냉각시킨 후, 2상 혼합물을 에틸 아세테이트로 3회 추출하였다. 추출물을 포화 수성 염화나트륨 용액으로 세척하고, 무수 황산마그네슘 상에서 건조시키고, 여과하고, 감압하에 농축시켜 건조시켜 표제 화합물을 금색 황색 발포체로서 수득하였다.1- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro in aqueous 2 M sodium carbonate solution (3 mL) and 1: 1 ethanol / toluene (12 mL) -1,3,5-triazin-2-yl) piperidin-4-one (1.0 g, 3.1 mmol), 4-aminophenylboronic acid, pinacol esters (1.0 g, 4.7 mmol) and tetrakis ( A suspension of triphenylphosphine) palladium (0.20 g, 0.17 mmol) was microwaved at 120 ° C. for 1 hour. After cooling, the biphasic mixture was extracted three times with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under reduced pressure to afford the title compound as a gold yellow foam.

MS (ES+) = 381.6 (M+H)+MS (ES +) = 381.6 (M + H) &lt; + &gt;

단계 4: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조:Step 4: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1,3 Preparation of, 5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea:

디클로로메탄 (30 mL) 중 조 1-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일)피페리딘-4-온 (대략 3.1 mmol) 및 트리에틸아민 (4 mL)의 혼합물을 트리포스겐 (0.71 g, 2.4 mmol)으로 처리하였다. 이어서, 혼합물을 테트라히드로푸란 (20 mL) 중 4-아미노피리딘 (1.8 g, 19 mmol)의 용액으로 처리하였다. 혼합물을 감압하에 농축시켜 건조시키고, 잔류물을 HPLC로 정제하여 표제 화합물을 그의 TFA 염으로서 수득하였다. MS (ES+) 501.2 (M+H)+Crude 1- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -1,3,5-tri in dichloromethane (30 mL) A mixture of azin-2-yl) piperidin-4-one (approximately 3.1 mmol) and triethylamine (4 mL) was treated with triposgen (0.71 g, 2.4 mmol). The mixture was then treated with a solution of 4-aminopyridine (1.8 g, 19 mmol) in tetrahydrofuran (20 mL). The mixture was concentrated under reduced pressure to dryness and the residue was purified by HPLC to afford the title compound as its TFA salt. MS (ES +) 501.2 (M + H) +

실시예 116: 1-{4-[4-(4-히드록시피페리딘-1-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 116 1- {4- [4- (4-hydroxypiperidin-1-yl) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1 Preparation of 3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea

1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (56 mg)를 메탄올/테트라히드로푸란 (1:1, 6 mL) 중에 녹이고, 혼합물을 0℃에서 수소화붕소나트륨 (10 mg)으로 처리하였다. 실온으로 가온시킨 후에, 혼합물을 잔류물로 농축시키고, 이어서 HPLC로 정제하여 표제 화합물을 그의 TFA 염으로서 수득하였다. MS (ES+) 503.0 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1,3,5- Triazine-2-yl) phenyl) -3- (pyridin-4-yl) ureaTFA (56 mg) is dissolved in methanol / tetrahydrofuran (1: 1, 6 mL) and the mixture is boron hydride at 0 ° C. Treated with sodium (10 mg). After warming to room temperature, the mixture was concentrated to the residue and then purified by HPLC to give the title compound as its TFA salt. MS (ES +) 503.0 (M + H) +

실시예 117: 1-(4-{4-[4-(벤즈일아미노)피페리딘-1-일]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 117 1- (4- {4- [4- (benzylamino) piperidin-1-yl] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea

디클로로메탄 (3 mL) 및 테트라히드로푸란 (3 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (85 mg)를 벤질아민 (0.030 mL)에 이어 빙초산 (0.016 mL) 및 나트륨 트리아세톡시보로히드라이드 (89 mg)로 처리하였다. 반응 완료 후, 메탄올을 첨가하고, 혼합물을 농축시켜 건조시켰다. 잔류물을 HPLC로 정제하여 표제 화합물을 그의 디-TFA 염으로서 수득하였다.1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-jade) in dichloromethane (3 mL) and tetrahydrofuran (3 mL) Sopiperidin-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) ureaTFA (85 mg) followed by benzylamine (0.030 mL) Treated with glacial acetic acid (0.016 mL) and sodium triacetoxyborohydride (89 mg). After completion of the reaction, methanol was added and the mixture was concentrated to dryness. The residue was purified by HPLC to give the title compound as its di-TFA salt.

MS (ES+) 592.3 (M+H)+MS (ES +) 592.3 (M + H) +

실시예 118: 1-(4-{4-[4-(메틸아미노)피페리딘-1-일]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 118: 1- (4- {4- [4- (methylamino) piperidin-1-yl] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) Preparation of -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea

테트라히드로푸란 (5 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (50 mg)를 메틸아민 (테트라히드로푸란 중 2.0 M 용액, 0.16 mL)에 이어, 빙초산 (0.009 mL) 및 나트륨 트리아세톡시보로히드라이드 (51 mg)로 처리하였다. 반응 완료 후, 메탄올을 첨가하고, 혼합물을 농축시켜 건조시켰다. 잔류물을 HPLC로 정제하여 표제 화합물을 그의 디-TFA 염으로서 수득하였다; MS (ES+) 516.3 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) in tetrahydrofuran (5 mL) ) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) ureaTFA (50 mg) was added to methylamine (2.0 M solution in tetrahydrofuran, 0.16 mL). Then treated with glacial acetic acid (0.009 mL) and sodium triacetoxyborohydride (51 mg). After completion of the reaction, methanol was added and the mixture was concentrated to dryness. The residue was purified by HPLC to give the title compound as its di-TFA salt; MS (ES +) 516.3 (M + H) +

실시예 119: 1-(4-{4-[4-(에틸아미노)피페리딘-1-일]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 119: 1- (4- {4- [4- (ethylamino) piperidin-1-yl] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) Preparation of -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea

테트라히드로푸란 (5 mL) 중 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (50 mg)를 에틸아민 (테트라히드로푸란 중 2.0 M 용액, 0.16 mL)에 이어, 빙초산 (0.009 mL) 및 나트륨 트리아세톡시보로히드라이드 (51 mg)로 처리하였다. 반응 완료 후, 메탄올을 첨가하고, 혼합물을 농축시켜 건조시켰다. 잔류물을 HPLC로 정제하여 표제 화합물을 그의 디-TFA 염으로서 수득하였다; MS (ES+) 530.3 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) in tetrahydrofuran (5 mL) ) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) ureaTFA (50 mg) in ethylamine (2.0 M solution in tetrahydrofuran, 0.16 mL) Then treated with glacial acetic acid (0.009 mL) and sodium triacetoxyborohydride (51 mg). After completion of the reaction, methanol was added and the mixture was concentrated to dryness. The residue was purified by HPLC to give the title compound as its di-TFA salt; MS (ES +) 530.3 (M + H) &lt; + &gt;

실시예 120: 1-{4-[4-(4-{[2-(디메틸아미노)에틸]아미노}피페리딘-1-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 120: 1- {4- [4- (4-{[2- (dimethylamino) ethyl] amino} piperidin-1-yl) -6- (8-oxa-3-azabicyclo [3.2. 1] Oct-3-yl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea

표제 화합물을 실시예 118에 요약된 절차에 따라, 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (50 mg)를 N,N-디메틸에틸렌디아민 (0.026 mL)과 반응시키고, HPLC로 정제하고, 그의 트리-TFA 염으로서 단리하여 제조하였다; MS (ES+) 573.7 (M+H)+.The title compound was purified according to the procedure outlined in Example 118: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperi Din-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) ureaTFA (50 mg) to N, N-dimethylethylenediamine (0.026 mL ), Purified by HPLC and isolated as its tri-TFA salt; MS (ES +) 573.7 (M + H) &lt; + &gt;.

실시예 121: 1-{4-[4-(4-모르폴린-4-일피페리딘-1-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 121 1- {4- [4- (4-morpholin-4-ylpiperidin-1-yl) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea

1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (50 mg)를 1-(2-아미노에틸)피롤리딘 (0.030 mL)과 반응시키고 실험 118에 언급된 바와 같은 절차에 따라, 표제 생성물을 그의 트리-TFA 염으로서 단리하였다; MS (ES+) 599.8 (M+H)+.1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1,3,5- Triazine-2-yl) phenyl) -3- (pyridin-4-yl) urea.TFA (50 mg) was reacted with 1- (2-aminoethyl) pyrrolidine (0.030 mL) and mentioned in Experiment 118. Following the procedure as described, the title product was isolated as its tri-TFA salt; MS (ES +) 599.8 (M + H) &lt; + &gt;.

실시예 122: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(4-메틸피페라진-1-일)피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조Example 122: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (4-methylpiperazin-1-yl) pi Preparation of Ferridin-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea

1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (40 mg) 및 1-메틸피페라진 (0.050 mL)을 반응시키고 실시에 118에 요약된 바와 같은 절차에 따라, HPLC 정제 후에 표제 화합물을 그의 트리-TFA 염으로서 단리하였다; MS (ES+) 585.9 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1,3,5- Triazine-2-yl) phenyl) -3- (pyridin-4-yl) urea.TFA (40 mg) and 1-methylpiperazine (0.050 mL) were reacted and following the procedure as outlined in Example 118 , After HPLC purification, the title compound was isolated as its tri-TFA salt; MS (ES +) 585.9 (M + H) &lt; + &gt;

실시예 123: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(2-히드록시에틸아미노)피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조Example 123: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (2-hydroxyethylamino) piperidine- Preparation of 1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea

1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (50 mg) 및 에탄올아민 (0.020 mL)으로부터 출발하여 실시에 118에 요약된 바와 같은 절차에 따라, HPLC 정제 후에 표제 화합물을 그의 디-TFA 염으로서 단리하였다. MS (ES+) 546.7 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1,3,5- HPLC purification, following the procedure as outlined in Example 118 starting from triazine-2-yl) phenyl) -3- (pyridin-4-yl) urea.TFA (50 mg) and ethanolamine (0.020 mL). The title compound was then isolated as its di-TFA salt. MS (ES +) 546.7 (M + H) &lt; + &gt;

실시예 124: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(2-모르폴리노에틸아미노)피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조Example 124 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (2-morpholinoethylamino) piperidine Preparation of -1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea

1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (50 mg) 및 1-(2-아미노에틸)모르폴린 (0.031 mL)으로부터 출발하여 실시에 118에 요약된 바와 같은 절차에 따라, HPLC 정제 후에 표제 화합물을 그의 트리-TFA 염으로서 단리하였다; MS (ES+) 615.9 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1,3,5- Triazine-2-yl) phenyl) -3- (pyridin-4-yl) urea.TFA (50 mg) and 1- (2-aminoethyl) morpholine (0.031 mL), summarized in Example 118 According to the procedure as described, after HPLC purification the title compound was isolated as its tri-TFA salt; MS (ES +) 615.9 (M + H) &lt; + &gt;

실시예 125: 메틸 2-(1-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)피페리딘-4-일아미노)아세테이트의 제조Example 125 Methyl 2- (1- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (3-pyridin-4-ylureido) Preparation of Phenyl) -1,3,5-triazin-2-yl) piperidin-4-ylamino) acetate

1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (50 mg) 및 글리신 메틸 에스테르 히드로클로라이드 (20 mg) 및 트리에틸아민 (10 방울)으로부터 출발하여 실시에 118에 요약된 바와 같은 절차에 따라, HPLC 정제 후에 표제 화합물을 그의 디-TFA 염으로서 단리하였다; MS (ES+) 574.8 (M+H)+.1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1,3,5- Triazine-2-yl) phenyl) -3- (pyridin-4-yl) urea.TFA (50 mg) and glycine methyl ester hydrochloride (20 mg) and triethylamine (10 drops) Following the procedure as summarized in the following, the title compound was isolated as its di-TFA salt after HPLC purification; MS (ES +) 574.8 (M + H) &lt; + &gt;.

실시예 126: 2-(1-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)피페리딘-4-일아미노)아세트아미드의 제조Example 126: 2- (1- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (3-pyridin-4-ylureido) phenyl ) -1,3,5-triazin-2-yl) piperidin-4-ylamino) acetamide

1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (50 mg) 및 글리신아미드 히드로클로라이드 (18 mg) 및 트리에틸아민 (10 방울)으로부터 출발하여 실시에 118에 요약된 바와 같은 절차에 따라, HPLC 정제 후에 표제 화합물을 그의 디-TFA 염으로서 단리하였다; MS (ES+) 559.8 (M+H)+1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1,3,5- Triazine-2-yl) phenyl) -3- (pyridin-4-yl) urea.TFA (50 mg) and glycineamide hydrochloride (18 mg) and triethylamine (10 drops) According to the procedure as outlined, the title compound was isolated as its di-TFA salt after HPLC purification; MS (ES +) 559.8 (M + H) &lt; + &gt;

실시예 127: Tert-부틸 2-(1-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)피페리딘-4-일아미노)아세테이트의 제조Example 127 Tert-butyl 2- (1- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (3-pyridin-4-ylurei) Fig.) Phenyl) -1,3,5-triazin-2-yl) piperidin-4-ylamino) acetate

1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-옥소피페리딘-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아·TFA (60 mg) 및 글리신 tert-부틸 에스테르 히드로클로라이드 (33 mg) 및 트리에틸아민 (10 방울)으로부터 출발하여 실시에 118에 요약된 바와 같은 절차에 따라, HPLC 정제 후에 표제 화합물을 그의 디-TFA 염으로서 단리하였다; MS (ES+) 616.9 (M+H)+.1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-oxopiperidin-1-yl) -1,3,5- Triazine-2-yl) phenyl) -3- (pyridin-4-yl) urea-TFA (60 mg) and glycine tert-butyl ester hydrochloride (33 mg) and triethylamine (10 drops) According to the procedure as summarized in at 118, the title compound was isolated as its di-TFA salt after HPLC purification; MS (ES +) 616.9 (M + H) &lt; + &gt;.

실시예 128: 2-(1-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)피페리딘-4-일아미노)아세트산의 제조Example 128: 2- (1- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (3-pyridin-4-ylureido) phenyl ) -1,3,5-triazin-2-yl) piperidin-4-ylamino) acetic acid

디클로로메탄 (3 mL) 중 tert-부틸 2-(1-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)피페리딘-4-일아미노)아세테이트 (28 mg)를 트리플루오로아세트산 (1 mL)으로 처리한 후에, 농축시켜 건조시켜 표제 화합물을 그의 TFA 염으로서 수득하였다.Tert-butyl 2- (1- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (3-pyridine-4) in dichloromethane (3 mL) -Ylureido) phenyl) -1,3,5-triazin-2-yl) piperidin-4-ylamino) acetate (28 mg) after treatment with trifluoroacetic acid (1 mL), concentrated Drying to give the title compound as its TFA salt.

MS (ES+) 560.2 (M+H)+.MS (ES +) 560.2 (M + H) &lt; + &gt;.

실시예 129: 4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아닐린의 제조; MS (ES+) 399.47 (M+H)+.Example 129: 4- [4- (1,4-Dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2 -Yl] aniline; MS (ES +) 399.47 (M + H) &lt; + &gt;.

실시예 130: 1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ES+) 519.58 (M+H)+.Example 130: 1- {4- [4- (1,4-Dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl-1,3,5-tree Preparation of azin-2-yl] phenyl} -3-pyridin-4-ylurea; MS (ES +) 519.58 (M + H) &lt; + &gt;.

실시예 131: 1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ES+) 519.58 (M+H)+.Example 131 1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl-1,3,5-tree Preparation of azin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ES +) 519.58 (M + H) &lt; + &gt;.

실시예 132: 1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-페닐우레아의 제조; MS (ES+) 518.59 (M+H)+.Example 132: 1- {4- [4- (1,4-Dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl-1,3,5-tree Preparation of azin-2-yl] phenyl} -3-phenylurea; MS (ES +) 518.59 (M + H) &lt; + &gt;.

실시예 133: 1-[4-(디메틸아미노)페닐]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ES+) 561.66 (M+H)+.Example 133: 1- [4- (dimethylamino) phenyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholine Preparation of -4-yl-1,3,5-triazin-2-yl] phenyl} urea; MS (ES +) 561.66 (M + H) &lt; + &gt;.

실시예 134: 1-(4-시아노페닐)-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ES+) 543.60 (M+H)+.Example 134: 1- (4-cyanophenyl) -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholine-4 Preparation of -yl-1,3,5-triazin-2-yl] phenyl} urea; MS (ES &lt; + &gt;) 543.60 (M + H) &lt; + &gt;.

실시예 135: 1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(2-메틸피리딘-4-일)우레아의 제조; MS (ES+) 533.61 (M+H)+Example 135: 1- {4- [4- (1,4-Dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl-1,3,5-tree Preparation of azin-2-yl] phenyl} -3- (2-methylpyridin-4-yl) urea; MS (ES +) 533.61 (M + H) &lt; + &gt;

실시예 136: 1-[2-(디메틸아미노)에틸]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ES+) 513.62 (M+H)+Example 136: 1- [2- (dimethylamino) ethyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholine Preparation of -4-yl-1,3,5-triazin-2-yl] phenyl} urea; MS (ES +) 513.62 (M + H) &lt; + &gt;

실시예 137: 1-[4-(4-모르폴린-4-일-6-퀴놀린-3-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조Example 137 1- [4- (4-morpholin-4-yl-6-quinolin-3-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-yl Manufacture of urea

Figure 112010076169004-pct00034
Figure 112010076169004-pct00034

실시예 138: 2-(디플루오로메틸)-1-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)-1H-벤즈이미다졸의 제조Example 138: 2- (difluoromethyl) -1- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazine- Preparation of 2-yl) -1H-benzimidazole

아세톤 (5 mL) 중 시아누르산 클로라이드 (922 mg, 5 mmol)의 용액을 얼음에 첨가하였다. 이어서, 수성 아세톤 중 8-옥사-3-아자비시클로[3.2.1]옥탄 히드로클로라이드 (750 mg, 5 mmol) 및 트리에틸아민 (2.1 mL, 15 mmol)의 용액을 첨가하였다. 20 분 후에 침전물을 수집하여 백색 분말 1.0 g을 얻고, 이것은 3-(4,6-디클로로-1,3,5-트리아진-2,4-디일)-8-옥사-3-아자비시클로[3.2.1]옥탄 및 3,3'-(6-클로로-1,3,5-트리아진-2,4-디일)비스(8-옥사-3-아자비시클로[3.2.1]옥탄)의 7:3 혼합물이었다. 상기 혼합물 (400 mg)을 DMF (2.5 mL) 중 2-(디플루오로메틸)-1H-벤조[d]이미다졸 (146 mg, 0.87 mmol) 및 K2CO3 (967 mg, 7 mmol)으로 18 시간 동안 처리한 다음, 8-옥사-3-아자비시클로[3.2.1]옥탄 히드로클로라이드 (150 mg)를 첨가하여, 1 시간 후에 HPLC로 정제한 후 3,3'-(6-(2-(디플루오로메틸)-1H-벤조[d]이미다졸-1-일)-1,3,5-트리아진-2,4-디일)비스(8-옥사-3-아자비시클로[3.2.1]옥탄)을 수득하였다. (M+H) 475.A solution of cyanuric chloride (922 mg, 5 mmol) in acetone (5 mL) was added to ice. Then a solution of 8-oxa-3-azabicyclo [3.2.1] octane hydrochloride (750 mg, 5 mmol) and triethylamine (2.1 mL, 15 mmol) in aqueous acetone was added. After 20 minutes the precipitate was collected to yield 1.0 g of a white powder, which was 3- (4,6-dichloro-1,3,5-triazine-2,4-diyl) -8-oxa-3-azabicyclo [3.2 .1] 7 of octane and 3,3 '-(6-chloro-1,3,5-triazine-2,4-diyl) bis (8-oxa-3-azabicyclo [3.2.1] octane) 3 mixtures. The mixture (400 mg) was converted to 2- (difluoromethyl) -1H-benzo [d] imidazole (146 mg, 0.87 mmol) and K 2 CO 3 (967 mg, 7 mmol) in DMF (2.5 mL). After 18 hours of treatment, 8-oxa-3-azabicyclo [3.2.1] octane hydrochloride (150 mg) was added, after 1 hour purification with HPLC followed by 3,3 '-(6- (2- (Difluoromethyl) -1H-benzo [d] imidazol-1-yl) -1,3,5-triazine-2,4-diyl) bis (8-oxa-3-azabicyclo [3.2.1 ] Octane) was obtained. (M + H) 475.

실시예 139: 2-(디플루오로메틸)-1-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]-1H-벤즈이미다졸의 제조Example 139: 2- (difluoromethyl) -1- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1, Preparation of 3,5-triazin-2-yl] -1 H-benzimidazole

아세톤/얼음 중 3-(4,6-디클로로-1,3,5-트리아진-2,4-디일)(8-옥사-3-아자비시클로[3.2.1]옥탄) (2.61 g, 10 mmol)의 교반 용액에 모르폴린 (900 mg, 12 mmol) 및 트리에틸아민 (5 ml)을 첨가하였다. 반응 혼합물을 실온에서 3 시간 동안 교반하였다. 분리된 백색 고체를 여과하고 물로 세척하였다. 수득된 조 생성물은 충분히 순수하고, 다음 단계에 정제 없이 사용하였다. 혼합물 (270 mg. 0.87 mmol)을 DMF (2.5 mL) 중 2-(디플루오로메틸)-1H-벤조[d]이미다졸 (146 mg, 0.87 mmol) 및 K2CO3 (967 mg, 7 mmol)으로 18 시간 동안 처리하여, HPLC로 정제한 후에 2-(디플루오로메틸)-1-[4-모르폴린-4-일-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]-1H-벤즈이미다졸을 수득하였다. (M+H) 445.3- (4,6-dichloro-1,3,5-triazine-2,4-diyl) (8-oxa-3-azabicyclo [3.2.1] octane) in acetone / ice (2.61 g, 10 mmol To a stirred solution of was added morpholine (900 mg, 12 mmol) and triethylamine (5 ml). The reaction mixture was stirred at room temperature for 3 hours. The separated white solid was filtered off and washed with water. The crude product obtained is sufficiently pure and used without purification in the next step. The mixture (270 mg. 0.87 mmol) was added 2- (difluoromethyl) -1H-benzo [d] imidazole (146 mg, 0.87 mmol) and K 2 CO 3 (967 mg, 7 mmol in DMF (2.5 mL). ) For 18 hours followed by purification by HPLC followed by 2- (difluoromethyl) -1- [4-morpholin-4-yl-6- (8-oxa-3-azabicyclo [3.2.1] Oct-3-3-yl) -1,3,5-triazine-2- * ¼] -1 H-benzimidazole was obtained. (M + H) 445.

실시예 140: 1-[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조; mp 212℃; MS (ESI) m/z 433.3.Example 140: 1- [4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4- Preparation of ilurea; mp 212 ° C .; MS (ESI) m / z 433.3.

실시예 141: 메틸 4-({[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트의 제조; mp 212℃; MS (ESI) m/z 490.2.Example 141: Methyl 4-({[4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} Preparation of amino) benzoate; mp 212 ° C .; MS (ESI) m / z 490.2.

실시예 142: 1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조; MS (ESI) m/z 561.6.Example 142 1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4- Preparation of methylpiperazin-1-yl) carbonyl] phenyl} urea; MS (ESI) m / z 561.6.

실시예 143: 4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드의 제조Example 143: 4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N Preparation of-(1-methylpiperidin-4-yl) benzamide

MS (ESI) m/z 575.6MS (ESI) m / z 575.6

실시예 144: 1-{4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-(2-피페리딘-1-일에톡시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 531.5Example 144: 1- {4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- (2-piperidin-1-ylethoxy) -1 Preparation of, 3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea; MS (ESI) m / z 531.5

실시예 145: 메틸(4-{4-[4-({[4-(4-메틸피페라진-1-일)페닐]카르바모일}아미노)페닐]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)카르바메이트의 제조; MS (ESI) m/z 650.7Example 145 Methyl (4- {4- [4-({[4- (4-methylpiperazin-1-yl) phenyl] carbamoyl} amino) phenyl] -6- (8-oxa-3- Preparation of azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl} phenyl) carbamate; MS (ESI) m / z 650.7

실시예 146: 1-시클로프로필-3-(4-{4-[4-({[4-(4-메틸피페라진-1-일)페닐]카르바모일}아미노)페닐]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 675.8Example 146 1-cyclopropyl-3- (4- {4- [4-({[4- (4-methylpiperazin-1-yl) phenyl] carbamoyl} amino) phenyl] -6- ( Preparation of 8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 675.8

실시예 147: N',N'''-{[6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2,4-디일]디-4,1-페닐렌}비스[1-[4-(4-메틸피페라진-1-일)페닐]우레아}의 제조; MS (ESI) m/z 809.9Example 147 N ', N' ''-{[6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine-2,4- Diyl] di-4,1-phenylene} bis [1- [4- (4-methylpiperazin-1-yl) phenyl] urea}; MS (ESI) m / z 809.9

실시예 148: 1-[4-(4-메틸피페라진-1-일)페닐]-3-{4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 712.8Example 148 1- [4- (4-methylpiperazin-1-yl) phenyl] -3- {4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 712.8

실시예 149: 1-(4-{4-[(2-아미노에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조Example 149: 1- (4- {4-[(2-aminoethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5 Preparation of -triazin-2-yl} phenyl) -3-pyridin-3-ylurea

Figure 112010076169004-pct00035
Figure 112010076169004-pct00035

실시예 150: 1-{4-[4-아닐리노-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조Example 150 1- {4- [4-anilino-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl ] Phenyl} -3-pyridin-3-ylurea

Figure 112010076169004-pct00036
Figure 112010076169004-pct00036

실시예 151: 4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피페리딘-1-일에틸)벤즈아미드의 제조Example 151: 4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (2 Preparation of -piperidin-1-ylethyl) benzamide

Figure 112010076169004-pct00037
Figure 112010076169004-pct00037

실시예 152: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(모르폴린-4-일카르보닐)페닐]우레아의 제조Example 152 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (morpholin-4-yl Preparation of Carbonyl) phenyl] urea

Figure 112010076169004-pct00038
Figure 112010076169004-pct00038

실시예 153: 1-(4-{4-[(2-히드록시에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 463.5.Example 153: 1- (4- {4-[(2-hydroxyethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3, Preparation of 5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 463.5.

실시예 154: 1-{4-[4-(아제티딘-3-일아미노)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 474.5Example 154: 1- {4- [4- (azetidin-3-ylamino) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5 Preparation of -triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 474.5

실시예 155: 1-(4-{4-[(2-모르폴린-4-일에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 532.6.Example 155: 1- (4- {4-[(2-morpholin-4-ylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl)- Preparation of 1,3,5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 532.6.

실시예 156: 1-(4-{4-[(3-아미노프로필)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 476.5.Example 156: 1- (4- {4-[(3-aminopropyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5 -Triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 476.5.

실시예 157: 1-(4-{4-[(4-시클로펜틸피페라진-1-일)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 571.7Example 157 1- (4- {4-[(4-cyclopentylpiperazin-1-yl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 571.7

실시예 158: 1-{4-[4-이소프로폭시-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아; MS (ESI) m/z 462.53Example 158: 1- {4- [4-isopropoxy-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine-2- Il] phenyl} -3-pyridin-4-ylurea; MS (ESI) m / z 462.53

실시예 159: 1-{4-[4-이소프로폭시-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조Example 159: 1- {4- [4-isopropoxy-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine-2- Preparation of yl] phenyl} -3- [4- (4-methylpiperazin-1-yl) phenyl] urea

실시예 160: 1-{4-[4-클로로-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 438.8Example 160: 1- {4- [4-chloro-6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl] Preparation of phenyl} -3-pyridin-4-ylurea; MS (ESI) m / z 438.8

실시예 161: 1-[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 391.5Example 161: Preparation of 1- [4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea; MS (ESI) m / z 391.5

실시예 162: 메틸 4-({[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트의 제조; MS (ESI) m/z 449.2.Example 162: of methyl 4-({[4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate Produce; MS (ESI) m / z 449.2.

실시예 163: 1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조; MS (ESI) m/z 584.7Example 163: 1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl ] Phenyl} -3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea; MS (ESI) m / z 584.7

실시예 164: 4-({[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드의 제조; MS (ESI) m/z 530.63.Example 164: 4-({[4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- ( Preparation of 1-methylpiperidin-4-yl) benzamide; MS (ESI) m / z 530.63.

실시예 165: N-[2-(디메틸아미노)에틸]-N-메틸-4-({[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드의 제조; MS (ESI) m/z 518.6Example 165 N- [2- (dimethylamino) ethyl] -N-methyl-4-({[4- (4-methyl-6-morpholin-4-yl-1,3,5-triazine- Preparation of 2-yl) phenyl] carbamoyl} amino) benzamide; MS (ESI) m / z 518.6

실시예 166: 1-[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조; MS (ESI) m/z 516.6.Example 166: 1- [4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpipepe Preparation of razin-1-yl) carbonyl] phenyl} urea; MS (ESI) m / z 516.6.

실시예 167: 1-(4-{[3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조Example 167: 1- (4-{[3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1 Preparation of 3,5-triazin-2-yl) phenyl] urea

Figure 112010076169004-pct00039
Figure 112010076169004-pct00039

실시예 168: 1-[4-({4-[2-(디메틸아미노)에틸]피페라진-1-일}카르보닐)페닐]-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조;Example 168: 1- [4-({4- [2- (dimethylamino) ethyl] piperazin-1-yl} carbonyl) phenyl] -3- [4- (4,6-dimorpholine-4 Preparation of -yl-1,3,5-triazin-2-yl) phenyl] urea;

Figure 112010076169004-pct00040
Figure 112010076169004-pct00040

실시예 169: 1-(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[(피페리딘-4-일메틸)아미노]-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 515.6Example 169: 1- (4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6-[(piperidin-4-ylmethyl) amino] -1 Preparation of, 3,5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 515.6

실시예 170: 1-(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[(2-피페리딘-4-일에틸)아미노]-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 529.65.Example 170: 1- (4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6-[(2-piperidin-4-ylethyl) amino] -1,3,5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 529.65.

실시예 171: 1-{4-[4-(3-메틸이미다졸리딘-1-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 487.5Example 171: 1- {4- [4- (3-methylimidazolidin-1-yl) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1 Preparation of, 3,5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 487.5

실시예 172: 1-{4-[4-(3-메틸테트라히드로피리미딘-1(2H)-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 501.6Example 172 1- {4- [4- (3-methyltetrahydropyrimidin-1 (2H) -yl) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 501.6

실시예 173: 1-{4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-(2-피페리딘-1-일에톡시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 530.6Example 173: 1- {4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- (2-piperidin-1-ylethoxy) -1 Preparation of, 3,5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 530.6

실시예 174: 1-(4-{4-[2-메톡시-1-(메톡시메틸)에톡시]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 521.58Example 174: 1- (4- {4- [2-methoxy-1- (methoxymethyl) ethoxy] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea; MS (ESI) m / z 521.58

실시예 175: 1-(4-{4-[2-메톡시-1-(메톡시메틸)에톡시]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조; MS (ESI) m/z 618.7.Example 175 1- (4- {4- [2-methoxy-1- (methoxymethyl) ethoxy] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl} phenyl) -3- [4- (4-methylpiperazin-1-yl) phenyl] urea; MS (ESI) m / z 618.7.

실시예 176: 2-히드록시에틸 (4-{4-[2-메톡시-1-(메톡시메틸)에톡시]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)카르바메이트의 제조; MS (ESI) m/z 489.53.Example 176: 2-hydroxyethyl (4- {4- [2-methoxy-1- (methoxymethyl) ethoxy] -6- (8-oxa-3-azabicyclo [3.2.1] oct- Preparation of 3-yl) -1,3,5-triazin-2-yl} phenyl) carbamate; MS (ESI) m / z 489.53.

실시예 177: 1-(4-{4-[2-메톡시-1-(메톡시메틸)에톡시]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-메틸우레아의 제조; MS (ESI) m/z 458.52.Example 177 1- (4- {4- [2-methoxy-1- (methoxymethyl) ethoxy] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl} phenyl) -3-methylurea; MS (ESI) m / z 458.52.

실시예 178: 1-시클로프로필-3-(4-{4-[2-메톡시-1-(메톡시메틸)에톡시]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 484.56.Example 178: 1-cyclopropyl-3- (4- {4- [2-methoxy-1- (methoxymethyl) ethoxy] -6- (8-oxa-3-azabicyclo [3.2.1] Preparation of oct-3-yl) -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 484.56.

실시예 179: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-피롤리딘-1-일피페리딘-1-일)카르보닐]페닐}우레아의 제조Example 179: 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-pyrrolidine Preparation of -1-ylpiperidin-1-yl) carbonyl] phenyl} urea

Figure 112010076169004-pct00041
Figure 112010076169004-pct00041

실시예 180: 1-{4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-(피페리딘-3-일메톡시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 516.61Example 180: 1- {4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- (piperidin-3-ylmethoxy) -1,3, Preparation of 5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 516.61

실시예 181: 1-{4-[4-(4-아미노부톡시)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 490.57Example 181 1- {4- [4- (4-aminobutoxy) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-tri Preparation of azin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 490.57

실시예 182: 1-{4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-(2-피페리딘-4-일에톡시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 530.63Example 182: 1- {4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- (2-piperidin-4-ylethoxy) -1 Preparation of, 3,5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 530.63

실시예 183: 1-{4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-(피페리딘-4-일메톡시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 516.61Example 183: 1- {4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- (piperidin-4-ylmethoxy) -1,3, Preparation of 5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 516.61

실시예 184: 4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산의 제조; MS (ESI) m/z 476.53Example 184: Preparation of 4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid; MS (ESI) m / z 476.53

실시예 185: N-[2-(디메틸아미노)에틸]-4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드의 제조; MS (ESI) m/z 562.6Example 185 N- [2- (dimethylamino) ethyl] -4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazine-2- Yl) phenyl] carbamoyl} amino) -N-methylbenzamide; MS (ESI) m / z 562.6

실시예 186: 1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 433.5Example 186: Preparation of 1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea; MS (ESI) m / z 433.5

실시예 187: N-[2-(디메틸아미노)에틸]-4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드의 제조; MS (ESI) m/z 548.67Example 187: N- [2- (dimethylamino) ethyl] -4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazine-2- Yl) phenyl] carbamoyl} amino) benzamide; MS (ESI) m / z 548.67

실시예 188: 메틸 4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트의 제조; MS (ESI) m/z 490.56.Example 188: of methyl 4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate Produce; MS (ESI) m / z 490.56.

실시예 189: 1-(4-{4-모르폴린-4-일-6-[(1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵트-5-일]-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 189: 1- (4- {4-morpholin-4-yl-6-[(1S, 4S) -2-oxa-5-azabicyclo [2.2.1] hept-5-yl] -1, Preparation of 3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea

Figure 112010076169004-pct00042
Figure 112010076169004-pct00042

실시예 190: 1-{4-[4-(메틸아미노)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 432.49.Example 190: 1- {4- [4- (methylamino) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine-2 -Yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 432.49.

실시예 191: 1-{4-[4-(에틸아미노)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 446.52Example 191: 1- {4- [4- (ethylamino) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine-2 -Yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 446.52

실시예 192: 1-{4-[4-(디메틸아미노)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 446.52.Example 192: 1- {4- [4- (dimethylamino) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine-2 -Yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 446.52.

실시예 193: 1-{4-[4-(이소프로필아미노)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 460.54Example 193: 1- {4- [4- (isopropylamino) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine- Preparation of 2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 460.54

실시예 194: 1-{4-[4-(디에틸아미노)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 474.57.Example 194 1- {4- [4- (diethylamino) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine- Preparation of 2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 474.57.

실시예 195: 4-({[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산의 제조; mp 204℃; MS (ESI) m/z 476.2;Example 195: 4-({[4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino ) Preparation of benzoic acid; mp 204 ° C; MS (ESI) m / z 476.2;

실시예 196: 1-[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조; mp 170℃; MS (ESI) m/z 558.2.Example 196 1- [4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4- [ Preparation of (4-methylpiperazin-1-yl) carbonyl] phenyl} urea; mp 170 ° C .; MS (ESI) m / z 558.2.

실시예 197: 4-({[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드의 제조Example 197: 4-({[4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino Preparation of) -N- [2- (dimethylamino) ethyl] -N-methylbenzamide

MS (ESI) m/z 280.7;MS (ESI) m / z 280.7;

실시예 198: 4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드의 제조Example 198: 4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [ Preparation of 2- (dimethylamino) ethyl] -N-methylbenzamide

실시예 199: 1-{4-[4-(1-에톡시비닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 447.499.Example 199 1- {4- [4- (1-ethoxyvinyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridine-4 Preparation of ilurea; MS (ESI) m / z 447.499.

실시예 200: 1-{4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 200 1- {4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridine- Preparation of 4-ylurea

Figure 112010076169004-pct00043
Figure 112010076169004-pct00043

실시예 201: 1-(디에틸카르바모일)-4-[({4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]피리디늄의 제조Example 201: 1- (diethylcarbamoyl) -4-[({4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8 -Yl) -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] pyridinium

Figure 112010076169004-pct00044
Figure 112010076169004-pct00044

실시예 202: 1-(4-{4-[에틸(메틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 460.54.Example 202 1- (4- {4- [ethyl (methyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-tri Preparation of azin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 460.54.

실시예 203: 1-{4-[4-(sec-부틸아미노)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 474.57.Example 203: 1- {4- [4- (sec-butylamino) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine -2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 474.57.

실시예 204: 1-{4-[4-{[2-히드록시-1-(히드록시메틸)에틸]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 492.54.Example 204: 1- {4- [4-{[2-hydroxy-1- (hydroxymethyl) ethyl] amino} -6- (8-oxa-3-azabicyclo [3.2.1] oct-3 -Yl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 492.54.

실시예 205: 1-(4-{4-[비스(2-히드록시에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 506.57Example 205: 1- (4- {4- [bis (2-hydroxyethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3 Preparation of, 5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 506.57

실시예 206: 1-(4-{4-[(1S,4S)-2,5-디아자비시클로[2.2.1]헵트-2-일]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 499.58.Example 206: 1- (4- {4-[(1S, 4S) -2,5-diazabicyclo [2.2.1] hept-2-yl] -6- (8-oxa-3-azabicyclo [ 3.2.1] preparation of oct-3-yl) -1,3,5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 499.58.

실시예 207: 1-{4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 592.71.Example 207: 1- {4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3-azabicyclo [3.2.1] oct- 3-yl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 592.71.

실시예 208: 1-(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[(4-피페라진-1-일페닐)아미노]-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 578.68.Example 208: 1- (4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6-[(4-piperazin-1-ylphenyl) amino]- Preparation of 1,3,5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 578.68.

실시예 209: 1-[4-(4-아세틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 419.406Example 209: Preparation of 1- [4- (4-acetyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea; MS (ESI) m / z 419.406

실시예 210: 1-(4-{4-모르폴린-4-일-6-[(1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵트-5-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-피롤리딘-1-일피페리딘-1-일)카르보닐]페닐}우레아의 제조;Example 210: 1- (4- {4-morpholin-4-yl-6-[(1S, 4S) -2-oxa-5-azabicyclo [2.2.1] hept-5-yl] -1, Preparation of 3,5-triazin-2-yl} phenyl) -3- {4-[(4-pyrrolidin-1-ylpiperidin-1-yl) carbonyl] phenyl} urea;

Figure 112010076169004-pct00045
Figure 112010076169004-pct00045

실시예 211: 메틸 4-[({4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트의 제조Example 211: Methyl 4-[({4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carba Moyl) amino] benzoate

Figure 112010076169004-pct00046
Figure 112010076169004-pct00046

실시예 212: 1-메틸-3-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 397.48.Example 212: 1-methyl-3- (4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1 Preparation of, 3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 397.48.

실시예 213: 1-시클로프로필-3-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 423.52.Example 213: 1-cyclopropyl-3- (4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl)- Preparation of 1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 423.52.

실시예 214: 1-(2-히드록시에틸)-3-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 427.51.Example 214: 1- (2-hydroxyethyl) -3- (4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct- Preparation of 3-yl) -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 427.51.

실시예 215: 1-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 460.54.Example 215: 1- (4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5 Preparation of -triazin-2-yl} phenyl) -3-pyridin-4-ylurea; MS (ESI) m / z 460.54.

실시예 216: 1-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-[6-(4-메틸피페라진-1-일)피리딘-3-일]우레아의 제조; MS (ESI) m/z 460.54.Example 216: 1- (4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5 -Triazin-2-yl} phenyl) -3- [6- (4-methylpiperazin-1-yl) pyridin-3-yl] urea; MS (ESI) m / z 460.54.

실시예 217: 1-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조; MS (ESI) m/z 557.70.Example 217: 1- (4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5 -Triazin-2-yl} phenyl) -3- [4- (4-methylpiperazin-1-yl) phenyl] urea; MS (ESI) m / z 557.70.

실시예 218: 1-{4-[(2,2-디메틸히드라지노)카르보닐]페닐}-3-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 545.65.Example 218: 1- {4-[(2,2-dimethylhydrazino) carbonyl] phenyl} -3- (4- {4-[(1-methylethyl) amino] -6- (8-oxa- Preparation of 3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 545.65.

실시예 219: 4-{[(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-피롤리딘-1-일벤즈아미드의 제조; MS (ESI) m/z 571.69.Example 219: 4-{[(4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3 , 5-triazin-2-yl} phenyl) carbamoyl] amino} -N-pyrrolidin-1-ylbenzamide; MS (ESI) m / z 571.69.

실시예 220: 1-{4-[2-(디메틸아미노)에톡시]페닐}-3-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 546.68.Example 220 1- {4- [2- (dimethylamino) ethoxy] phenyl} -3- (4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabi Preparation of cyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 546.68.

실시예 221: 1-[4-(히드록시메틸)페닐]-3-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 489.58Example 221: 1- [4- (hydroxymethyl) phenyl] -3- (4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1 ] Oct-3-yl) -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 489.58

실시예 222: 1-[4-(2-히드록시에틸)페닐]-3-(4-{4-[(1-메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 503.61.Example 222: 1- [4- (2-hydroxyethyl) phenyl] -3- (4- {4-[(1-methylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2 .1] preparation of oct-3-yl) -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 503.61.

실시예 223: 1-{4-[4-(1-히드록시에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 421.46.Example 223: 1- {4- [4- (1-hydroxyethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridine-4 Preparation of ilurea; MS (ESI) m / z 421.46.

실시예 224: 1-[4-(4,6-디-3-옥사-8-아자비시클로[3.2.1]옥트-8-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 514.59.Example 224: 1- [4- (4,6-Di-3-oxa-8-azabicyclo [3.2.1] oct-8-yl-1,3,5-triazin-2-yl) phenyl] Preparation of 3-pyridin-4-ylurea; MS (ESI) m / z 514.59.

실시예 225: 메틸 4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트의 제조; MS (ESI) m/z 462.51Example 225: Methyl 4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate Produce; MS (ESI) m / z 462.51

실시예 226: 메틸 4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트의 제조; MS (ESI) m/z 516.55.Example 226: Methyl 4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazine- Preparation of 2-yl] phenyl} carbamoyl) amino] benzoate; MS (ESI) m / z 516.55.

실시예 227: 4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산의 제조; MS (ESI) m/z 502.53Example 227: 4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazine-2 -Yl] phenyl} carbamoyl) amino] benzoic acid; MS (ESI) m / z 502.53

실시예 228: 1-(4-{4-모르폴린-4-일-6-[2-(피리딘-4-일아미노)에틸]-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 228: 1- (4- {4-morpholin-4-yl-6- [2- (pyridin-4-ylamino) ethyl] -1,3,5-triazin-2-yl} phenyl) Preparation of 3-Pyridin-4-ylurea

Figure 112010076169004-pct00047
Figure 112010076169004-pct00047

실시예 229: 1-[4-(4-메틸피페라진-1-일)페닐]-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 229: 1- [4- (4-methylpiperazin-1-yl) phenyl] -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [ 3.2.1] Oct-8-yl) -1,3,5-triazin-2-yl] phenyl} urea

Figure 112010076169004-pct00048
Figure 112010076169004-pct00048

실시예 230: 1-(4-아세틸페닐)-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 230: 1- (4-acetylphenyl) -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl) Preparation of -1,3,5-triazin-2-yl] phenyl} urea

Figure 112010076169004-pct00049
Figure 112010076169004-pct00049

실시예 231: 4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[2-(디메틸아미노)에틸]벤즈아미드의 제조; MS (ESI) m/z 546.676.Example 231: 4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [ Preparation of 2- (dimethylamino) ethyl] benzamide; MS (ESI) m / z 546.676.

실시예 232: 1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조Example 232: 1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpipepe Preparation of Razin-1-yl) carbonyl] phenyl} urea

MS (ESI) m/z 559.4.MS (ESI) m / z 559.4.

실시예 233: 4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산의 제조; MS (ESI) m/z 448.483Example 233: Preparation of 4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid; MS (ESI) m / z 448.483

실시예 234: 1-메틸-3-{4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-(9-옥사-3,7-디아자비시클로[3.3.1]논-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 234 1-methyl-3- {4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- (9-oxa-3,7-diazabi Preparation of cyclo [3.3.1] non-3-yl) -1,3,5-triazin-2-yl] phenyl} urea

Figure 112010076169004-pct00050
Figure 112010076169004-pct00050

실시예 235: 1-{4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-(9-옥사-3,7-디아자비시클로[3.3.1]논-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조Example 235: 1- {4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- (9-oxa-3,7-diazabicyclo [3.3. 1] non-3-yl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea

Figure 112010076169004-pct00051
Figure 112010076169004-pct00051

실시예 236: 1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조; MS (ESI) m/z 531.1.Example 236: 1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpipepe Preparation of razin-1-yl) carbonyl] phenyl} urea; MS (ESI) m / z 531.1.

실시예 237: N-[2-(디메틸아미노)에틸]-4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드의 제조Example 237: N- [2- (dimethylamino) ethyl] -4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) Preparation of Phenyl] carbamoyl} amino) benzamide

실시예 238: 1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 558.711Example 238: 1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4-ethyl-6-morpholin-4-yl- Preparation of 1,3,5-triazin-2-yl) phenyl] urea; MS (ESI) m / z 558.711

실시예 239: 1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아의 제조; MS (ESI) m/z 462.554.Example 239: 1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl ] Preparation of urea; MS (ESI) m / z 462.554.

실시예 240: 4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드의 제조; MS (ESI) m/z 586.721.Example 240: 4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazine-2 -Yl] phenyl} carbamoyl) amino] -N- [2- (dimethylamino) ethyl] -N-methylbenzamide; MS (ESI) m / z 586.721.

실시예 241: 1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아의 제조; MS (ESI) m/z 586.741.Example 241 1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-{[4- (dimethyl Preparation of amino) piperidin-1-yl] carbonyl} phenyl) urea; MS (ESI) m / z 586.741.

실시예 242: N-[2-(디메틸아미노)에틸]-4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드의 제조; MS (ESI) m/z 532.649.Example 242 N- [2- (dimethylamino) ethyl] -4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) Phenyl] carbamoyl} amino) -N-methylbenzamide; MS (ESI) m / z 532.649.

실시예 243: N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드의 제조; MS (ESI) m/z 534.62.Example 243: N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl ) Phenyl] carbamoyl} amino) -N-methylbenzamide; MS (ESI) m / z 534.62.

실시예 244: N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드의 제조; MS (ESI) m/z 520.60.Example 244 N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl ) Phenyl] carbamoyl} amino) benzamide; MS (ESI) m / z 520.60.

실시예 245: 4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸-N-[2-(메틸아미노)에틸]벤즈아미드의 제조; MS (ESI) m/z 520.60.Example 245: 4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- Preparation of methyl-N- [2- (methylamino) ethyl] benzamide; MS (ESI) m / z 520.60.

실시예 246: 1-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조; MS (ESI) m/z 532.61.Example 246: 1- [4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methyl Preparation of piperazin-1-yl) carbonyl] phenyl} urea; MS (ESI) m / z 532.61.

실시예 247: 1-{4-[(3,3-디메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 546.63.Example 247 1- {4-[(3,3-dimethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-methoxy-6-morpholin-4-yl-1 Preparation of, 3,5-triazin-2-yl) phenyl] urea; MS (ESI) m / z 546.63.

실시예 248: 4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피페리딘-1-일에틸)벤즈아미드의 제조; MS (ESI) m/z 560.66.Example 248: 4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- Preparation of (2-piperidin-1-ylethyl) benzamide; MS (ESI) m / z 560.66.

실시예 249: 1-(4-에테닐페닐)-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 514.3;Example 249 1- (4-ethenylphenyl) -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl ) -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 514.3;

Figure 112010076169004-pct00052
Figure 112010076169004-pct00052

실시예 250: 1-{4-[(4-메틸피페라진-1-일)메틸]페닐}-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조;Example 250: 1- {4-[(4-methylpiperazin-1-yl) methyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (3-oxa-8- Preparation of azabicyclo [3.2.1] oct-8-yl) -1,3,5-triazin-2-yl] phenyl} urea;

Figure 112010076169004-pct00053
Figure 112010076169004-pct00053

실시예 251: 4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[4-(4-메틸피페라진-1-일)페닐]벤즈아미드의 제조; MS (ESI) m/z 621.77.Example 251: 4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [ Preparation of 4- (4-methylpiperazin-1-yl) phenyl] benzamide; MS (ESI) m / z 621.77.

실시예 252: 1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-({[2-(디메틸아미노)에틸]아미노}메틸)페닐]우레아의 제조; MS (ESI) m/z 532.71.Example 252: 1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4-({[2- ( Preparation of dimethylamino) ethyl] amino} methyl) phenyl] urea; MS (ESI) m / z 532.71.

실시예 253: 4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[4-(4-메틸피페라진-1-일)페닐]벤즈아미드의 제조; MS (ESI) m/z 649.82.Example 253: 4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [ Preparation of 4- (4-methylpiperazin-1-yl) phenyl] benzamide; MS (ESI) m / z 649.82.

실시예 254: 1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)메틸]페닐}우레아의 제조; MS (ESI) m/z 544.728.Example 254 1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpipepe Preparation of razin-1-yl) methyl] phenyl} urea; MS (ESI) m / z 544.728.

실시예 255: 1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-포르밀페닐)우레아의 제조; MS (ESI) m/z 461.2.Example 255 of 1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-formylphenyl) urea Produce; MS (ESI) m / z 461.2.

실시예 256: tert-부틸(1R,4R)-5-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)-2,5-디아자비시클로[2.2.1]헵탄-2-카르복실레이트의 제조; mp 192℃; MS (ESI) m/z 574.3.Example 256 tert-butyl (1R, 4R) -5- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3, Preparation of 5-triazin-2-yl) -2,5-diazabicyclo [2.2.1] heptane-2-carboxylate; mp 192 ° C .; MS (ESI) m / z 574.3.

실시예 257: tert-부틸 (1R,4R)-5-[4-(4-{[(4-아세틸페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]-2,5-디아자비시클로[2.2.1]헵탄-2-카르복실레이트의 제조; mp 202℃; MS (ESI) m/z 615.3;Example 257 tert-butyl (1R, 4R) -5- [4- (4-{[(4-acetylphenyl) carbamoyl] amino} phenyl) -6-morpholin-4-yl-1,3 Preparation of, 5-triazin-2-yl] -2,5-diazabicyclo [2.2.1] heptane-2-carboxylate; mp 202 ° C .; MS (ESI) m / z 615.3;

실시예 258: 1-(4-{4-[(2-메톡시에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 476.54Example 258: 1- (4- {4-[(2-methoxyethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3, Preparation of 5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 476.54

실시예 259: 1-{4-[4-{[(1S)-2-히드록시-1-메틸에틸]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 476.54.Example 259: 1- {4- [4-{[(1S) -2-hydroxy-1-methylethyl] amino} -6- (8-oxa-3-azabicyclo [3.2.1] oct-3 -Yl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 476.54.

실시예 260: 1-{4-[4-{[(1R)-2-히드록시-1-메틸에틸]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 476.54.Example 260: 1- {4- [4-{[(1R) -2-hydroxy-1-methylethyl] amino} -6- (8-oxa-3-azabicyclo [3.2.1] oct-3 -Yl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 476.54.

실시예 261: 1-(4-{4-[(2-히드록시-1,1-디메틸에틸)아미노]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 490.57.Example 261: 1- (4- {4-[(2-hydroxy-1,1-dimethylethyl) amino] -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl} phenyl) -3-pyridin-3-ylurea; MS (ESI) m / z 490.57.

실시예 262: 1-{4-[4-(tert-부틸아미노)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조; MS (ESI) m/z 474.57.Example 262: 1- {4- [4- (tert-butylamino) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazine -2-yl] phenyl} -3-pyridin-3-ylurea; MS (ESI) m / z 474.57.

실시예 263: 4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(피리딘-2-일메틸)벤즈아미드의 제조;Example 263: 4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (pyridine Preparation of 2-ylmethyl) benzamide;

Figure 112010076169004-pct00054
Figure 112010076169004-pct00054

Figure 112010076169004-pct00055
Figure 112010076169004-pct00055

실시예 264: 1-[4-(4,6-디-3-옥사-8-아자비시클로[3.2.1]옥트-8-일-1,3,5-트리아진-2-일)페닐]-3-(4-피페라진-1-일페닐)우레아의 제조;Example 264 1- [4- (4,6-di-3-oxa-8-azabicyclo [3.2.1] oct-8-yl-1,3,5-triazin-2-yl) phenyl] Preparation of -3- (4-piperazin-1-ylphenyl) urea;

Figure 112010076169004-pct00056
Figure 112010076169004-pct00056

실시예 265: 1-[4-(4,6-디-3-옥사-8-아자비시클로[3.2.1]옥트-8-일-1,3,5-트리아진-2-일)페닐]-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조;Example 265: 1- [4- (4,6-Di-3-oxa-8-azabicyclo [3.2.1] oct-8-yl-1,3,5-triazin-2-yl) phenyl] Preparation of -3- [4- (4-methylpiperazin-1-yl) phenyl] urea;

Figure 112010076169004-pct00057
Figure 112010076169004-pct00057

실시예 266: 1-{4-[2-(디메틸아미노)에톡시]페닐}-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 266: 1- {4- [2- (dimethylamino) ethoxy] phenyl} -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2 .1] Oct-8-yl) -1,3,5-triazin-2-yl] phenyl} urea

Figure 112010076169004-pct00058
Figure 112010076169004-pct00058

실시예 267: 1-(4-{4-[2-(1,3-디옥산-2-일)에틸]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 267: 1- (4- {4- [2- (1,3-dioxan-2-yl) ethyl] -6-morpholin-4-yl-1,3,5-triazine-2- Preparation of phenyl) -3-pyridin-4-ylurea

Figure 112010076169004-pct00059
Figure 112010076169004-pct00059

실시예 268: 1-(4-{4-[2,5-비스(히드록시메틸)피롤리딘-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 268: 1- (4- {4- [2,5-bis (hydroxymethyl) pyrrolidin-1-yl] -6-morpholin-4-yl-1,3,5-triazine- Preparation of 2-yl} phenyl) -3-pyridin-4-ylurea

Figure 112010076169004-pct00060
Figure 112010076169004-pct00060

실시예 269: 4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-{4-[2-(디메틸아미노)에톡시]페닐}벤즈아미드의 제조; MS (ESI) m/z 638.773.Example 269: 4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- { Preparation of 4- [2- (dimethylamino) ethoxy] phenyl} benzamide; MS (ESI) m / z 638.773.

실시예 270: 1-{4-[(4-벤질피페리딘-1-일)카르보닐]페닐}-3-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 633.821.Example 270 1- {4-[(4-benzylpiperidin-1-yl) carbonyl] phenyl} -3- [4- (4-butyl-6-morpholin-4-yl-1,3 Preparation of, 5-triazin-2-yl) phenyl] urea; MS (ESI) m / z 633.821.

실시예 271: 4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드의 제조; MS (ESI) m/z 545.3.Example 271: 4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- ( Preparation of 1-methylpiperidin-4-yl) benzamide; MS (ESI) m / z 545.3.

실시예 272: 4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드의 제조; MS (ESI) m/z 573.4.Example 272: 4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- ( Preparation of 1-methylpiperidin-4-yl) benzamide; MS (ESI) m / z 573.4.

실시예 273: 1-{4-[4-(6-히드록시-3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 504.551.Example 273: 1- {4- [4- (6-hydroxy-3-oxa-8-azabicyclo [3.2.1] oct-8-yl) -6-morpholin-4-yl-1,3 Preparation of, 5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea; MS (ESI) m / z 504.551.

실시예 274: 1-(4-{4-[3-(디메틸아미노)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 462.56.Example 274 1- (4- {4- [3- (dimethylamino) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridine Preparation of -4-ylurea; MS (ESI) m / z 462.56.

실시예 275: 1-[4-(4-{3-[(1-메틸에틸)아미노]프로필}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 476.59.Example 275: 1- [4- (4- {3-[(1-methylethyl) amino] propyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl ] -3-pyridin-4-ylurea; MS (ESI) m / z 476.59.

실시예 276: 1-{4-[4-모르폴린-4-일-6-(3-피롤리딘-1-일프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 488.60.Example 276 1- {4- [4-morpholin-4-yl-6- (3-pyrrolidin-1-ylpropyl) -1,3,5-triazin-2-yl] phenyl}- Preparation of 3-pyridin-4-ylurea; MS (ESI) m / z 488.60.

실시예 277: 1-(4-{4-[3-(4-메틸피페라진-1-일)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 517.64.Example 277 1- (4- {4- [3- (4-methylpiperazin-1-yl) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl } Phenyl) -3-pyridin-4-ylurea; MS (ESI) m / z 517.64.

실시예 278: 1-{4-[4-(3-{[2-(디메틸아미노)에틸]아미노}프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 505.63.Example 278: 1- {4- [4- (3-{[2- (dimethylamino) ethyl] amino} propyl) -6-morpholin-4-yl-1,3,5-triazine-2- Preparation of the one] phenyl} -3-pyridin-4-ylurea; MS (ESI) m / z 505.63.

실시예 279: 1-{4-[4-(3-히드록시프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 435.49.Example 279: 1- {4- [4- (3-hydroxypropyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridine-4 Preparation of ilurea; MS (ESI) m / z 435.49.

실시예 280: 1-{4-[4-모르폴린-4-일-6-(3-옥소프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 433.47.Example 280: 1- {4- [4-morpholin-4-yl-6- (3-oxopropyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-4- Preparation of ilurea; MS (ESI) m / z 433.47.

실시예 281: tert-부틸-7-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)-9-옥사-3,7-디아자비시클로[3.3.1]노난-3-카르복실레이트의 제조Example 281 tert-butyl-7- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazine- Preparation of 2-yl) -9-oxa-3,7-diazabicyclo [3.3.1] nonan-3-carboxylate

Figure 112010076169004-pct00061
Figure 112010076169004-pct00061

실시예 282: 1-{4-[4-(6,8-디옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 282: 1- {4- [4- (6,8-dioxa-3-azabicyclo [3.2.1] oct-3-yl) -6-morpholin-4-yl-1,3,5 Preparation of -triazin-2-yl] phenyl} -3-pyridin-4-ylurea

Figure 112010076169004-pct00062
Figure 112010076169004-pct00062

실시예 283: 1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아의 제조; MS (ESI) m/z 612.759.Example 283 1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl ] Phenyl} -3- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) urea; MS (ESI) m / z 612.759.

실시예 284: 4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]벤즈아미드의 제조; MS (ESI) m/z 572.694.Example 284: 4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazine-2 -Yl] phenyl} carbamoyl) amino] -N- [2- (dimethylamino) ethyl] benzamide; MS (ESI) m / z 572.694.

실시예 285: 1-[4-(4,6-디-3-옥사-8-아자비시클로[3.2.1]옥트-8-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)메틸]페닐}우레아의 제조; MS (ESI) m/z 625.78Example 285: 1- [4- (4,6-di-3-oxa-8-azabicyclo [3.2.1] oct-8-yl-1,3,5-triazin-2-yl) phenyl] Preparation of -3- {4-[(4-methylpiperazin-1-yl) methyl] phenyl} urea; MS (ESI) m / z 625.78

실시예 286: N-[4-(4,6-디-3-옥사-8-아자비시클로[3.2.1]옥트-8-일-1,3,5-트리아진-2-일)페닐]피페라진-1-카르복스아미드의 제조; MS (ESI) m/z 506.61Example 286: N- [4- (4,6-di-3-oxa-8-azabicyclo [3.2.1] oct-8-yl-1,3,5-triazin-2-yl) phenyl] Preparation of piperazine-1-carboxamide; MS (ESI) m / z 506.61

실시예 287: 1-[4-(4,6-디-3-옥사-8-아자비시클로[3.2.1]옥트-8-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아의 제조; MS (ESI) m/z 543.63.Example 287: 1- [4- (4,6-di-3-oxa-8-azabicyclo [3.2.1] oct-8-yl-1,3,5-triazin-2-yl) phenyl] Preparation of -3- [4- (hydroxymethyl) phenyl] urea; MS (ESI) m / z 543.63.

실시예 288: 1-[4-(4,6-디-3-옥사-8-아자비시클로[3.2.1]옥트-8-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(메틸아미노)메틸]페닐}우레아의 제조; MS (ESI) m/z 556.67.Example 288 1- [4- (4,6-di-3-oxa-8-azabicyclo [3.2.1] oct-8-yl-1,3,5-triazin-2-yl) phenyl] Preparation of -3- {4-[(methylamino) methyl] phenyl} urea; MS (ESI) m / z 556.67.

실시예 289: 1-{4-[2-(디메틸아미노)에톡시]페닐}-3-[4-(4,6-디-3-옥사-8-아자비시클로[3.2.1]옥트-8-일-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 600.73.Example 289: 1- {4- [2- (dimethylamino) ethoxy] phenyl} -3- [4- (4,6-di-3-oxa-8-azabicyclo [3.2.1] oct-8 Preparation of -yl-1,3,5-triazin-2-yl) phenyl] urea; MS (ESI) m / z 600.73.

실시예 290: 1-{4-[4-모르폴린-4-일-6-(9-옥사-3,7-디아자비시클로[3.3.1]논-3-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 503.57.Example 290: 1- {4- [4-morpholin-4-yl-6- (9-oxa-3,7-diazabicyclo [3.3.1] non-3-yl) -1,3,5 Preparation of -triazin-2-yl] phenyl} -3-pyridin-4-ylurea; MS (ESI) m / z 503.57.

실시예 291: 1-{4-[4-(7-메틸-9-옥사-3,7-디아자비시클로[3.3.1]논-3-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 517.60.Example 291: 1- {4- [4- (7-methyl-9-oxa-3,7-diazabicyclo [3.3.1] non-3-yl) -6-morpholin-4-yl-1 Preparation of, 3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea; MS (ESI) m / z 517.60.

실시예 292: 1-{4-[4-(7-아세틸-9-옥사-3,7-디아자비시클로[3.3.1]논-3-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 545.61.Example 292: 1- {4- [4- (7-acetyl-9-oxa-3,7-diazabicyclo [3.3.1] non-3-yl) -6-morpholin-4-yl-1 Preparation of, 3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea; MS (ESI) m / z 545.61.

실시예 293: 1-(4-{4-[7-(메틸술포닐)-9-옥사-3,7-디아자비시클로[3.3.1]논-3-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 581.66.Example 293: 1- (4- {4- [7- (methylsulfonyl) -9-oxa-3,7-diazabicyclo [3.3.1] non-3-yl] -6-morpholine-4 Preparation of -yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea; MS (ESI) m / z 581.66.

실시예 294: 1-[4-(4-메틸피페라진-1-일)페닐]-3-[4-(4-모르폴린-4-일-6-프로필-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 517.4.Example 294: 1- [4- (4-methylpiperazin-1-yl) phenyl] -3- [4- (4-morpholin-4-yl-6-propyl-1,3,5-triazine Preparation of -2-yl) phenyl] urea; MS (ESI) m / z 517.4.

실시예 295: 1-{4-[2-(디메틸아미노)에톡시]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 492.2.Example 295 1- {4- [2- (dimethylamino) ethoxy] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazine- Preparation of 2-yl) phenyl] urea; MS (ESI) m / z 492.2.

실시예 296: 1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조; MS (ESI) m/z 503.Example 296: 1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (4-methylpiperazin Preparation of -1-yl) phenyl] urea; MS (ESI) m / z 503.

실시예 297: 1-[4-(4-메틸피페라진-1-일)페닐]-3-{4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 530.701.Example 297 1- [4- (4-methylpiperazin-1-yl) phenyl] -3- {4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3 Preparation of, 5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 530.701.

실시예 298: 1-{4-[(3,3-디메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 544.684.Example 298: 1- {4-[(3,3-dimethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1, Preparation of 3,5-triazin-2-yl) phenyl] urea; MS (ESI) m / z 544.684.

실시예 299: 4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸아제티딘-3-일)벤즈아미드의 제조Example 299: 4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- ( Preparation of 1-methylazetidin-3-yl) benzamide

Figure 112010076169004-pct00063
Figure 112010076169004-pct00063

실시예 300: 메틸 4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트의 제조Example 300 Methyl 4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) Preparation of Amino] benzoate

Figure 112010076169004-pct00064
Figure 112010076169004-pct00064

실시예 301: 4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산의 제조Example 301: 4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino ] Production of benzoic acid

MS (ESI) m/z 463.3.MS (ESI) m / z 463.3.

실시예 302: tert-부틸-(1R,4R)-5-{4-[4-({[4-(1-히드록시에틸)페닐]카르바모일}아미노)페닐]-6-모르폴린-4-일-1,3,5-트리아진-2-일}-2,5-디아자비시클로[2.2.1]헵탄-2-카르복실레이트의 제조Example 302 tert-butyl- (1R, 4R) -5- {4- [4-({[4- (1-hydroxyethyl) phenyl] carbamoyl} amino) phenyl] -6-morpholine- Preparation of 4-yl-1,3,5-triazin-2-yl} -2,5-diazabicyclo [2.2.1] heptane-2-carboxylate

MS (ESI) m/z 617.4.MS (ESI) m / z 617.4.

실시예 303: 1-[4-(4-메틸피페라진-1-일)페닐]-3-{4-[4-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 303 1- [4- (4-methylpiperazin-1-yl) phenyl] -3- {4- [4- (3-oxa-8-azabicyclo [3.2.1] oct-8-yl ) -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl] phenyl} urea

Figure 112010076169004-pct00065
Figure 112010076169004-pct00065

실시예 304: 1-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조; MS (ESI) m/z 544.66.Example 304: 1- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- {4- [ Preparation of (4-methylpiperazin-1-yl) carbonyl] phenyl} urea; MS (ESI) m / z 544.66.

실시예 305: N-[2-(디메틸아미노)에틸]-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조; MS (ESI) m/z 532.65.Example 305: N- [2- (dimethylamino) ethyl] -4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazine -2-yl] phenyl} carbamoyl) amino] benzamide; MS (ESI) m / z 532.65.

실시예 306: N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조; MS (ESI) m/z 546.68.Example 306: N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3, 5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide; MS (ESI) m / z 546.68.

실시예 307: N-(1-메틸아제티딘-3-일)-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조; MS (ESI) m/z 530.63.Example 307: N- (1-methylazetidin-3-yl) -4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5- Preparation of triazin-2-yl] phenyl} carbamoyl) amino] benzamide; MS (ESI) m / z 530.63.

실시예 308: 1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 572.72.Example 308 1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4- (1-methylethyl) -6-morpholine Preparation of -4-yl-1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 572.72.

실시예 309: 4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-피리딘-4-일벤즈아미드의 제조; MS (ESI) m/z 538.61.Example 309: 4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino ] -N-pyridin-4-ylbenzamide; MS (ESI) m / z 538.61.

실시예 310: 4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-피리딘-3-일벤즈아미드의 제조; MS (ESI) m/z 538.61.Example 310: 4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino ] -N-pyridin-3-ylbenzamide; MS (ESI) m / z 538.61.

실시예 311: N-시클로부틸-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조; MS (ESI) m/z 515.62.Example 311 N-cyclobutyl-4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} Carbamoyl) amino] benzamide; MS (ESI) m / z 515.62.

실시예 312: 1-{4-[4,6-디-(1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵트-5-일-1,3,5-트리아진-2-일]페닐}-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조; MS (ESI) m/z 583.70.Example 312: 1- {4- [4,6-di- (1S, 4S) -2-oxa-5-azabicyclo [2.2.1] hept-5-yl-1,3,5-triazine- Preparation of 2-yl] phenyl} -3- [4- (4-methylpiperazin-1-yl) phenyl] urea; MS (ESI) m / z 583.70.

실시예 313: 1-{4-[4,6-디-(1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵트-5-일-1,3,5-트리아진-2-일]페닐}-3-(4-피페라진-1-일페닐)우레아의 제조; MS (ESI) m/z 569.67.Example 313: 1- {4- [4,6-Di- (1S, 4S) -2-oxa-5-azabicyclo [2.2.1] hept-5-yl-1,3,5-triazine- Preparation of 2-yl] phenyl} -3- (4-piperazin-1-ylphenyl) urea; MS (ESI) m / z 569.67.

실시예 314: 1-{4-[4,6-디-(1R,4R)-2-옥사-5-아자비시클로[2.2.1]헵트-5-일-1,3,5-트리아진-2-일]페닐}-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조; MS (ESI) m/z 583.70.Example 314: 1- {4- [4,6-di- (1R, 4R) -2-oxa-5-azabicyclo [2.2.1] hept-5-yl-1,3,5-triazine- Preparation of 2-yl] phenyl} -3- [4- (4-methylpiperazin-1-yl) phenyl] urea; MS (ESI) m / z 583.70.

실시예 315: 1-(2-플루오로에틸)-3-{4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 561.6.Example 315 1- (2-fluoroethyl) -3- {4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3 Preparation of azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 561.6.

실시예 316: 1-시클로프로필-3-{4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 555.71.Example 316: 1-cyclopropyl-3- {4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3-azabicyclo [3.2 .1] preparation of oct-3-yl) -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 555.71.

실시예 317: 1-메틸-3-{4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 529.67.Example 317: 1-methyl-3- {4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3-azabicyclo [3.2. 1] oct-3-yl) -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 529.67.

실시예 318: 4-[({4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조; MS (ESI) m/z 634.745.Example 318: 4-[({4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3-azabicyclo [3.2.1] Oct-3-yl) -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide; MS (ESI) m / z 634.745.

실시예 319: 1-{4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-페닐우레아; MS (ESI) m/z 591.72.Example 319: 1- {4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3-azabicyclo [3.2.1] oct- 3-yl) -1,3,5-triazin-2-yl] phenyl} -3-phenylurea; MS (ESI) m / z 591.72.

실시예 320: 1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-페닐피페리딘-1-일)카르보닐]페닐}우레아의 제조Example 320: 1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-phenylpy Preparation of Ferridin-1-yl) carbonyl] phenyl} urea

MS m/z 08-301429LMS.MS m / z 08-301429LMS.

실시예 321: 4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(피리딘-4-일메틸)벤즈아미드의 제조Example 321: 4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- ( Preparation of Pyridin-4-ylmethyl) benzamide

MS (ESI) m/z 539.4;MS (ESI) m / z 539.4;

MS (ESI) m/z 270.2.MS (ESI) m / z 270.2.

실시예 322: 1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 558.711.Example 322 1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4- (2-methylpropyl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 558.711.

실시예 323: 1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 586.765.Example 323 1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4- (2-methylpropyl) -6-morpholine Preparation of -4-yl-1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 586.765.

실시예 324: N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조; MS (ESI) m/z 560.727.Example 324: N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3, 5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide; MS (ESI) m / z 560.727.

실시예 325: 1-메틸-3-(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[(4-피페라진-1-일페닐)아미노]-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 515.62.Example 325: 1-methyl-3- (4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6-[(4-piperazin-1-ylphenyl ) Amino] -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 515.62.

실시예 326: 1-시클로프로필-3-(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[(4-피페라진-1-일페닐)아미노]-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 541.66.Example 326: 1-cyclopropyl-3- (4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6-[(4-piperazin-1-yl Phenyl) amino] -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 541.66.

실시예 327: 1-(2-플루오로에틸)-3-(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[(4-피페라진-1-일페닐)아미노]-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 547.64.Example 327 1- (2-fluoroethyl) -3- (4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6-[(4-pipe Preparation of razin-1-ylphenyl) amino] -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 547.64.

실시예 328: 1-(2-히드록시에틸)-3-(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[(4-피페라진-1-일페닐)아미노]-1,3,5-트리아진-2-일}페닐)우레아의 제조; MS (ESI) m/z 545.65.Example 328: 1- (2-hydroxyethyl) -3- (4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6-[(4-pipe Preparation of razin-1-ylphenyl) amino] -1,3,5-triazin-2-yl} phenyl) urea; MS (ESI) m / z 545.65.

실시예 329: 4-{[(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[(4-피페라진-1-일페닐)아미노]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드의 제조; MS (ESI) m/z 620.72.Example 329: 4-{[(4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6-[(4-piperazin-1-ylphenyl) amino ] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide; MS (ESI) m / z 620.72.

실시예 330: 1-(4-{4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-[(4-피페라진-1-일페닐)아미노]-1,3,5-트리아진-2-일}페닐)-3-페닐우레아의 제조; MS (ESI) m/z 577.69.Example 330: 1- (4- {4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6-[(4-piperazin-1-ylphenyl) amino]- Preparation of 1,3,5-triazin-2-yl} phenyl) -3-phenylurea; MS (ESI) m / z 577.69.

실시예 331: 1-메틸-3-{4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 529.67.Example 331: 1-methyl-3- {4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3-azabicyclo [3.2. 1] oct-3-yl) -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 529.67.

실시예 332: 1-시클로프로필-3-{4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 555.71.Example 332: 1-cyclopropyl-3- {4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3-azabicyclo [3.2 .1] preparation of oct-3-yl) -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 555.71.

실시예 333: 1-(2-플루오로에틸)-3-{4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 561.69.Example 333 1- (2-fluoroethyl) -3- {4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3 Preparation of azabicyclo [3.2.1] oct-3-yl) -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 561.69.

실시예 334: 4-[({4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-일]페닐}카르바모일)아미노]벤즈아미드의 제조; MS (ESI) m/z 634.745.Example 334: 4-[({4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3-azabicyclo [3.2.1] Preparation of oct-3-yl) -1,3,5-triazin-yl] phenyl} carbamoyl) amino] benzamide; MS (ESI) m / z 634.745.

실시예 335: 1-{4-[4-{[4-(4-메틸피페라진-1-일)페닐]아미노}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}-3-페닐우레아의 제조; MS (ESI) m/z 591.72;Example 335: 1- {4- [4-{[4- (4-methylpiperazin-1-yl) phenyl] amino} -6- (8-oxa-3-azabicyclo [3.2.1] oct- 3-yl) -1,3,5-triazin-2-yl] phenyl} -3-phenylurea; MS (ESI) m / z 591.72;

실시예 336: 1-(2,3'-비피리딘-4-일)-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 336: 1- (2,3'-bipyridin-4-yl) -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1 ] Oct-8-yl) -1,3,5-triazin-2-yl] phenyl} urea

Figure 112010076169004-pct00066
Figure 112010076169004-pct00066

실시예 337: 1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아의 제조Example 337: 1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- {4-[( Preparation of 4-methylpiperazin-1-yl) carbonyl] phenyl} urea

MS (ESI) m/z 593.5.MS (ESI) m / z 593.5.

실시예 338: N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조; MS (ESI) m/z 595.5.Example 338: N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5 -Triazin-2-yl] phenyl} carbamoyl) amino] benzamide; MS (ESI) m / z 595.5.

실시예 339: 1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 339 1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- {4- [4- (4-methylphenyl) -6-morpholin-4-yl- Preparation of 1,3,5-triazin-2-yl] phenyl} urea

MS (ESI) m/z 593.4.MS (ESI) m / z 593.4.

실시예 340: 1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조. MS (ESI) m/z 468.3.Example 340: 1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-yl Preparation of Urea. MS (ESI) m / z 468.3.

실시예 341: 1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 531.4.Example 341: 1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3, Preparation of 5-triazin-2-yl) phenyl] urea; MS (ESI) m / z 531.4.

실시예 342: 4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산의 제조, MS (ESI) m/z 511.4.Example 342: 4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] Preparation of benzoic acid, MS (ESI) m / z 511.4.

실시예 343: 1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조; MS (ESI) m/z 565.4.Example 343: 1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- [4- (4 Preparation of -methylpiperazin-1-yl) phenyl] urea; MS (ESI) m / z 565.4.

실시예 344: 메틸 4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트의 제조; MS (ESI) m/z 525.4.Example 344 Methyl 4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino ] Preparation of benzoate; MS (ESI) m / z 525.4.

실시예 345: 1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 578.745Example 345: 1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-morpholin-4-yl-6-phenyl-1,3, Preparation of 5-triazin-2-yl) phenyl] urea; MS (ESI) m / z 578.745

실시예 346: 1-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아의 제조; MS (ESI) m/z 454.1.Example 346: Preparation of 1- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea; MS (ESI) m / z 454.1.

(2S,5R)-피롤리딘-2,5-디일디메탄올 히드로클로라이드의 제조Preparation of (2S, 5R) -pyrrolidine-2,5-diyldimethanol hydrochloride

((2S,5R)-1-벤질피롤리딘-2,5-디일)디메탄올 (2.2 g, 10 mmol)을 에탄올/테트라히드로푸란 (200 mL, 1:1) 중에 용해시키고, 혼합물을 10％ 탄소상 팔라듐 (250 mg)으로 처리하였다. 현탁액을 수소 50 psi 하에서 수소 소비가 그칠 때까지 진탕시켰다. 혼합물을 에탄올로 용리하는 셀라이트™ 규조토 패드를 통해 여과하였다. 여과물을 농축시켜 건조시켜 표제 화합물을 금색 오일로서 수득하고, 이것은 장기간 저장 시에 고체화되었다. MS (ES+) = 132.2 (M+H)+ ((2S, 5R) -1-benzylpyrrolidine-2,5-diyl) dimethanol (2.2 g, 10 mmol) is dissolved in ethanol / tetrahydrofuran (200 mL, 1: 1) and the mixture is 10 Treated with% palladium on carbon (250 mg). The suspension was shaken under 50 psi of hydrogen until hydrogen consumption ceased. The mixture was filtered through a pad of Celite ™ diatomaceous earth eluting with ethanol. The filtrate was concentrated to dryness to afford the title compound as gold oil, which solidified on long term storage. MS (ES + ) = 132.2 (M + H) +

((2S,5R)-1-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)피롤리딘-2,5-디일)디메탄올의 제조Preparation of ((2S, 5R) -1- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) pyrrolidine-2,5-diyl) dimethanol

아세톤 (40 mL) 중 2,4-디클로로-6-(4-니트로페닐)-1,3,5-트리아진 (2.2 g, 8.0 mmol)의 현탁액을 자기 교반된 빙수 (60 mL)에 첨가하였다. 혼합물을 아세톤/물 (20 mL, 3:1) 중 (2S,5R)-피롤리딘-2,5-디일디메탄올 히드로클로라이드 (1.0 g, 6.0 mmol)의 용액에 이어 물 (12 mL) 중 탄산수소나트륨 (1.0 g, 12 mmol)의 현탁액으로 처리하였다. 0℃에서 30 분 교반한 후에, 혼합물을 물 (3 mL) 중 추가량의 (2S,5R)-피롤리딘-2,5-디일디메탄올 히드로클로라이드 (0.26 g, 1.6 mmol)에 이어 물 (5 mL) 중 탄산수소나트륨 (0.35 g)으로 처리하였다. 현탁액을 밤새 교반되도록 하면서, 실온으로 회복시켰다. 표제 화합물을 뷰흐너 여과로 단리하고, 물로 세척하고, 하우스 진공 하에 건조시켰다. 질량 분석법에 의한 화합물 확인은 에탄올 중에서 ((2S,5R)-1-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)피롤리딘-2,5-디일)디메탄올과 과량 모르폴린과의 반응 생성물의 분석을 통해 달성하였다. MS (ES+) = 417.2 (M + 모르폴린 - Cl)+ A suspension of 2,4-dichloro-6- (4-nitrophenyl) -1,3,5-triazine (2.2 g, 8.0 mmol) in acetone (40 mL) was added to magnetic stirred ice water (60 mL). . The mixture was poured into a solution of (2S, 5R) -pyrrolidine-2,5-diyldimethanol hydrochloride (1.0 g, 6.0 mmol) in acetone / water (20 mL, 3: 1) followed by water (12 mL) Treated with a suspension of sodium bicarbonate (1.0 g, 12 mmol). After 30 min stirring at 0 ° C., the mixture was added with an additional amount of (2S, 5R) -pyrrolidine-2,5-diyldimethanol hydrochloride (0.26 g, 1.6 mmol) in water (3 mL) followed by water ( 5 mL) in sodium bicarbonate ¨¨ (0.35 g). The suspension was allowed to stir overnight, then returned to room temperature. The title compound was isolated by Buchner filtration, washed with water and dried under house vacuum. Compound identification by mass spectrometry was carried out in ((2S, 5R) -1- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) pyrrolidine-2 in ethanol. This was achieved through analysis of the reaction product of, 5-diyl) dimethanol with excess morpholine. MS (ES + ) = 417.2 (M + morpholine-Cl) +

((2S,5R)-1-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)피롤리딘-2,5-디일)디메탄올의 제조((2S, 5R) -1- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (4-nitrophenyl) -1,3,5-triazine Preparation of 2-yl) pyrrolidin-2,5-diyl) dimethanol

에탄올 (13 mL) 중 ((2S,5R)-1-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)피롤리딘-2,5-디일)디메탄올 (0.91 g, 2.5 mmol), 3-옥사-8-아자비시클로[3.2.1]옥탄 히드로클로라이드 (0.37 g, 2.5 mmol)의 현탁액을 트리에틸아민 (1 mL)으로 처리하고, 마이크로파 반응기에서 20 분 동안 130℃에서 가열하였다. 반응 혼합물을 자동화 플래쉬 크로마토그래피 (메탄올/클로로포름)로 정제하여 표제 화합물을 경질 복숭아색 발포체로서 수득하였다. MS (ES+) = 443.2 (M+H)+ ((2S, 5R) -1- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) pyrrolidine-2,5- in ethanol (13 mL) A suspension of diyl) dimethanol (0.91 g, 2.5 mmol), 3-oxa-8-azabicyclo [3.2.1] octane hydrochloride (0.37 g, 2.5 mmol) was treated with triethylamine (1 mL) and microwave Heated at 130 ° C. for 20 minutes in the reactor. The reaction mixture was purified by automated flash chromatography (methanol / chloroform) to afford the title compound as a light peach foam. MS (ES + ) = 443.2 (M + H) +

8-(4-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄의 제조8- (4-((2S, 5R) -2,5-bis ((tert-butyldimethylsilyloxy) methyl) pyrrolidin-1-yl) -6- (4-nitrophenyl) -1,3, Preparation of 5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2.1] octane

디클로로메탄 (15 mL) 중 ((2S,5R)-1-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)피롤리딘-2,5-디일)디메탄올 (대략 2.7 mmol)의 용액을 tert-부틸 디메틸 클로로실란 (1.0 g, 6.8 mmol) 및 이미다졸 (0.55 g, 8.1 mmol)로 순서대로 처리하였다. 생성된 현탁액을 실온에서 밤새 교반한 다음, 물로 켄칭하였다. 수성상을 디클로로메탄으로 3회 추출하였다. 합한 추출물을 무수 황산마그네슘 상에서 건조시키고, 여과하고, 감압하에 농축시켜 건조시켰다. 조 잔류물을 자동화 플래쉬 크로마토그래피 (헥산/에틸 아세테이트)로 정제하여 표제 물질을 수득하였다. MS (ES+) = 671.4 (M+H)+ ((2S, 5R) -1- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (4-nitrophenyl) -1 in dichloromethane (15 mL) A solution of 3,5-triazin-2-yl) pyrrolidine-2,5-diyl) dimethanol (approximately 2.7 mmol) was added to tert-butyl dimethyl chlorosilane (1.0 g, 6.8 mmol) and imidazole (0.55 g, 8.1 mmol) in that order. The resulting suspension was stirred at rt overnight and then quenched with water. The aqueous phase was extracted three times with dichloromethane. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The crude residue was purified by automated flash chromatography (hexane / ethyl acetate) to afford the title material. MS (ES + ) = 671.4 (M + H) +

4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-1,3,5-트리아진-2-일)아닐린의 제조4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((2S, 5R) -2,5-bis ((tert-butyldimethylsilyloxy) methyl Preparation of Pyrrolidin-1-yl) -1,3,5-triazin-2-yl) aniline

테트라히드로푸란 (20 mL) 중 차콜상 팔라듐 (10％, 50 mg) 및 8-(4-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.55 g, 1.2 mmol)의 현탁액을 수소 풍선 하에 밤새 교반하였다. 혼합물을 셀라이트™ 규조토 패드를 통해 여과하고, 감압하에 농축시켜 표제 화합물을 황갈색 발포체로서 수득하였다 (0.42 g, 80％). MS (ES+) = 642.4 (M+H)+ Palladium charcoal (10%, 50 mg) and 8- (4-((2S, 5R) -2,5-bis ((tert-butyldimethylsilyloxy) methyl) pyrrolidine in tetrahydrofuran (20 mL) -1-yl) -6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2.1] octane (0.55 g, 1.2 mmol) The suspension of was stirred overnight under a hydrogen balloon. The mixture was filtered through a pad of Celite ™ diatomaceous earth and concentrated under reduced pressure to give the title compound as a tan foam (0.42 g, 80%). MS (ES + ) = 642.4 (M + H) +

실시예 347: 1-(4-{4-[(2R,5S)-2,5-비스(히드록시메틸)피롤리딘-1-일]-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 347: 1- (4- {4-[(2R, 5S) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl] -6- (3-oxa-8-azabicyclo [ 3.2.1] Preparation of oct-8-yl) -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea

디클로로메탄 (4 mL) 중 4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-1,3,5-트리아진-2-일)아닐린 (0.16 mmol)의 용액을 트리에틸아민 (1.6 mmol, 210 μL), 및 디클로로메탄 (500 μL) 중 트리포스겐 (24 mg, 0.08 mmol) 용액으로 순서대로 처리하였다. 5 분 후에, 혼합물을 따뜻한 테트라히드로푸란 중 4-아미노피리딘 (45 mg, 0.48 mmol)의 용액으로 처리하였다. 1 시간 후, 반응 혼합물을 메탄올로 켄칭하고, 농축시켜 건조시켰다. 조 잔류물을 메탄올 중 포화 염화수소 용액으로 처리하였다. 탈실릴화의 완료에 따라, 혼합물을 농축시켜 건조시키고, 잔류물을 25 분에 걸쳐 5％ 아세토니트릴/95％의 0.1％ 수성 트리플루오로아세트산에서 50％ 아세토니트릴의 구배 용리로 진행하는 페노메넥스 프로디지(Phenomenex Prodigy) 컬럼를 사용하는 역상 고성능 액체 크로마토그래피로 정제하였다. 농축 후, 표제 화합물을 그의 트리플루오로아세트산 염으로서 수득하였다 (132 mg). MS (ES+) = 533.3 (M+H)+ 4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((2S, 5R) -2,5-bis ((tert) in dichloromethane (4 mL) A solution of -butyldimethylsilyloxy) methyl) pyrrolidin-1-yl) -1,3,5-triazin-2-yl) aniline (0.16 mmol) with triethylamine (1.6 mmol, 210 μL), and Treated sequentially with a solution of triphosgen (24 mg, 0.08 mmol) in dichloromethane (500 μL). After 5 minutes, the mixture was treated with a solution of 4-aminopyridine (45 mg, 0.48 mmol) in warm tetrahydrofuran. After 1 h, the reaction mixture was quenched with methanol, concentrated to dryness. The crude residue was treated with saturated hydrogen chloride solution in methanol. Upon completion of desilylation, the mixture was concentrated to dryness and the residue proceeded to a gradient elution of 50% acetonitrile in 5% acetonitrile / 95% 0.1% aqueous trifluoroacetic acid over 25 minutes. Purification by reverse phase high performance liquid chromatography using a Phenomenex Prodigy column. After concentration, the title compound was obtained as its trifluoroacetic acid salt (132 mg). MS (ES + ) = 533.3 (M + H) +

실시예 348: 1-(4-{4-[(2R,5S)-2,5-비스(히드록시메틸)피롤리딘-1-일]-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일}페닐)-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조Example 348: 1- (4- {4-[(2R, 5S) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl] -6- (3-oxa-8-azabicyclo [ 3.2.1] Oct-8-yl) -1,3,5-triazin-2-yl} phenyl) -3- [4- (4-methylpiperazin-1-yl) phenyl] urea

디클로로메탄 (4 mL) 중 4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-1,3,5-트리아진-2-일)아닐린 (0.16 mmol)의 용액을 트리에틸아민 (1.6 mmol, 210 μL), 및 디클로로메탄 (500 μL) 중 트리포스겐 (24 mg, 0.08 mmol) 용액으로 순서대로 처리하였다. 5 분 후에, 혼합물을 4-(4-메틸피페라진-1-일)아닐린 (61 mg, 0.32 mmol)으로 처리하였다. 1 시간 후, 반응 혼합물을 메탄올로 켄칭하고, 농축시켜 건조시켰다. 조 잔류물을 메탄올 중 포화 염화수소 용액으로 처리하였다. 탈실릴화 완료에 따라, 혼합물을 농축시켜 건조시키고, 잔류물을 25 분에 걸쳐 5％ 아세토니트릴/95％의 0.1％ 수성 트리플루오로아세트산에서 50％ 아세토니트릴의 구배 용리로 진행하는 페노메넥스 프로디지 컬럼를 사용하는 역상 고성능 액체 크로마토그래피로 정제하였다. 농축 후, 표제 화합물을 그의 트리플루오로아세트산 염으로서 수득하였다 (100 mg). MS (ES+) = 630.4 (M+H)+ 4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((2S, 5R) -2,5-bis ((tert) in dichloromethane (4 mL) A solution of -butyldimethylsilyloxy) methyl) pyrrolidin-1-yl) -1,3,5-triazin-2-yl) aniline (0.16 mmol) with triethylamine (1.6 mmol, 210 μL), and Treated sequentially with a solution of triphosgen (24 mg, 0.08 mmol) in dichloromethane (500 μL). After 5 minutes, the mixture was treated with 4- (4-methylpiperazin-1-yl) aniline (61 mg, 0.32 mmol). After 1 h, the reaction mixture was quenched with methanol, concentrated to dryness. The crude residue was treated with saturated hydrogen chloride solution in methanol. Upon completion of desilylation, the mixture was concentrated to dryness and the residue proceeded to a gradient elution of 50% acetonitrile in 5% acetonitrile / 95% 0.1% aqueous trifluoroacetic acid over 25 minutes. Purification by reverse phase high performance liquid chromatography using a Prodigy column. After concentration, the title compound is obtained as its trifluoroacetic acid salt (100 mg). MS (ES + ) = 630.4 (M + H) +

실시예 349: 1-(6-클로로피리딘-3-일)-3-{4-[4-모르폴린-4-일-6-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조.Example 349 1- (6-Chloropyridin-3-yl) -3- {4- [4-morpholin-4-yl-6- (3-oxa-8-azabicyclo [3.2.1] oct- 8-yl) -1,3,5-triazin-2-yl] phenyl} urea.

Figure 112010076169004-pct00067
Figure 112010076169004-pct00067

실시예 350: 1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아의 제조; MS (ESI) m/z 614.8Example 350: 1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetra Preparation of hydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea; MS (ESI) m / z 614.8

실시예 351: 1-(4-아미노페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아의 제조; MS (ESI) m/z 477.1.Example 351: Preparation of 1- (4-aminophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea; MS (ESI) m / z 477.1.

실시예 352: N-[4-({[4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-N2,N2-디메틸글리신아미드의 제조Example 352 N- [4-({[4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazine-2 -Yl) phenyl] carbamoyl} amino) phenyl] -N2, N2-dimethylglycinamide

4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)아닐린 (50 mg, 0.127 mmol)을 디클로로메탄 (1.5 mL) 및 트리에틸아민 (0.120 mL) 중에 용해시키고, 디클로로메탄 (0.5 mL) 중 트리포스겐 (17 mg)의 용액에 첨가하였다. 5 분 동안 교반한 후에 N-(4-아미노페닐)-N2,N2-디메틸글리신아미드 (27 mg, 0.14 mmol)를 첨가하였다. 길슨 HPLC로 정제하여 표제 화합물을 TFA 염으로서 수득하였다: 31.8 mg (35％) (M+H) m/z 614.3.4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazin-2-yl) aniline (50 mg, 0.127 mmol) It was dissolved in dichloromethane (1.5 mL) and triethylamine (0.120 mL) and added to a solution of triphosgen (17 mg) in dichloromethane (0.5 mL). After stirring for 5 minutes N- (4-aminophenyl) -N2, N2-dimethylglycinamide (27 mg, 0.14 mmol) was added. Purification by Gilson HPLC gave the title compound as TFA salt: 31.8 mg (35%) (M + H) m / z 614.3.

실시예 353: N-[4-({[4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-2-피롤리딘-1-일아세트아미드의 제조Example 353: N- [4-({[4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazine-2 -Yl) phenyl] carbamoyl} amino) phenyl] -2-pyrrolidin-1-ylacetamide

4-(4,6-디-8-옥사-3-아자비시클로[3.2.1]옥트-3-일-1,3,5-트리아진-2-일)아닐린 (50 mg, 0.127 mmol)을 디클로로메탄 (1.5 mL) 및 트리에틸아민 (0.120 mL) 중에 용해시키고, 디클로로메탄 (0.5 mL) 중 트리포스겐 (17 mg)의 용액에 첨가하였다. 5 분 동안 교반한 후에 N-(4-아미노페닐)-2-피롤리딘-1-일아세트아미드 (30 mg, 0.14 mmol)를 첨가하고, 길슨 HPLC로 정제하여 표제 화합물을 TFA 염으로서 수득하였다: 63.1 mg (66％) (M+H) m/z 640.3.4- (4,6-di-8-oxa-3-azabicyclo [3.2.1] oct-3-yl-1,3,5-triazin-2-yl) aniline (50 mg, 0.127 mmol) It was dissolved in dichloromethane (1.5 mL) and triethylamine (0.120 mL) and added to a solution of triphosgen (17 mg) in dichloromethane (0.5 mL). After stirring for 5 minutes N- (4-aminophenyl) -2-pyrrolidin-1-ylacetamide (30 mg, 0.14 mmol) was added and purified by Gilson HPLC to afford the title compound as a TFA salt. : 63.1 mg (66%) (M + H) m / z 640.3.

실시예 354: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(피페라진-1-일)페닐아미노)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아의 제조Example 354: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (piperazin-1-yl) phenylamino)- Preparation of 1,3,5-triazin-2-yl) phenyl) -3-methylurea

반응식 1에 나타낸 바와 같이, 제2의 친핵성 방향족 치환 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노페닐)피페라진-1-카르복실레이트를 사용하여 제조하였다. 메틸아민을 사용하는 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 516.3.As shown in Scheme 1, a commercially available tert-butyl 4- (4-aminophenyl) piperazine-1-carboxylate was prepared in the second nucleophilic aromatic substitution step. Following urea formation using methylamine, the Boc-piperazine intermediate was treated with TFA to afford the title compound. (M + H) 516.3.

실시예 355: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(피페라진-1-일)페닐아미노)-1,3,5-트리아진-2-일)페닐)-3-시클로프로필우레아의 제조Example 355 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (piperazin-1-yl) phenylamino)- Preparation of 1,3,5-triazin-2-yl) phenyl) -3-cyclopropylurea

반응식 1에 나타낸 바와 같이, 제2의 친핵성 방향족 치환 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노페닐)피페라진-1-카르복실레이트를 사용하여 제조하였다. 시클로프로필아민을 사용하는 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 542.3.As shown in Scheme 1, a commercially available tert-butyl 4- (4-aminophenyl) piperazine-1-carboxylate was prepared in the second nucleophilic aromatic substitution step. Following urea formation using cyclopropylamine, the Boc-piperazine intermediate was treated with TFA to afford the title compound. (M + H) 542.3.

실시예 356: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(피페라진-1-일)페닐아미노)-1,3,5-트리아진-2-일)페닐)-3-(2-플루오로에틸)우레아의 제조Example 356: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (piperazin-1-yl) phenylamino)- Preparation of 1,3,5-triazin-2-yl) phenyl) -3- (2-fluoroethyl) urea

반응식 1에 나타낸 바와 같이, 제2의 친핵성 방향족 치환 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노페닐)피페라진-1-카르복실레이트를 사용하여 제조하였다. 2-플루오로에틸아민을 사용하는 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 548.3.As shown in Scheme 1, a commercially available tert-butyl 4- (4-aminophenyl) piperazine-1-carboxylate was prepared in the second nucleophilic aromatic substitution step. Following urea formation using 2-fluoroethylamine, the Boc-piperazine intermediate was treated with TFA to afford the title compound. (M + H) 548.3.

실시예 357: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(피페라진-1-일)페닐아미노)-1,3,5-트리아진-2-일)페닐)-3-(2-히드록시에틸)우레아의 제조Example 357: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (piperazin-1-yl) phenylamino)- Preparation of 1,3,5-triazin-2-yl) phenyl) -3- (2-hydroxyethyl) urea

반응식 1에 나타낸 바와 같이, 제2의 친핵성 방향족 치환 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노페닐)피페라진-1-카르복실레이트를 사용하여 제조하였다. 2-아미노에탄올을 사용하는 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 546.3.As shown in Scheme 1, a commercially available tert-butyl 4- (4-aminophenyl) piperazine-1-carboxylate was prepared in the second nucleophilic aromatic substitution step. Following urea formation using 2-aminoethanol, the Boc-piperazine intermediate was treated with TFA to afford the title compound. (M + H) 546.3.

실시예 358: 4-(3-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(피페라진-1-일)페닐아미노)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드의 제조Example 358: 4- (3- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (piperazin-1-yl) phenyl Preparation of amino) -1,3,5-triazin-2-yl) phenyl) ureido) benzamide

반응식 1에 나타낸 바와 같이, 제2의 친핵성 방향족 치환 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노페닐)피페라진-1-카르복실레이트를 사용하여 제조하였다. 4-아미노벤즈아미드를 사용하는 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 621.3.As shown in Scheme 1, a commercially available tert-butyl 4- (4-aminophenyl) piperazine-1-carboxylate was prepared in the second nucleophilic aromatic substitution step. Following urea formation using 4-aminobenzamide, the Boc-piperazine intermediate was treated with TFA to afford the title compound. (M + H) 621.3.

실시예 359: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-(피페라진-1-일)페닐아미노)-1,3,5-트리아진-2-일)페닐)-3-페닐우레아의 제조Example 359: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4- (piperazin-1-yl) phenylamino)- Preparation of 1,3,5-triazin-2-yl) phenyl) -3-phenylurea

반응식 1에 나타낸 바와 같이, 제2의 친핵성 방향족 치환 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노페닐)피페라진-1-카르복실레이트를 사용하여 제조하였다. 아닐린을 사용하는 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 578.3.As shown in Scheme 1, a commercially available tert-butyl 4- (4-aminophenyl) piperazine-1-carboxylate was prepared in the second nucleophilic aromatic substitution step. Following urea formation using aniline, the Boc-piperazine intermediate was treated with TFA to afford the title compound. (M + H) 578.3.

실시예 360: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(피페리딘-4-일아미노)-1,3,5-트리아진-2-일)페닐)-3-에틸우레아의 제조Example 360: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (piperidin-4-ylamino) -1,3, Preparation of 5-triazin-2-yl) phenyl) -3-ethylurea

반응식 1에 나타낸 바와 같이, 제2의 친핵성 방향족 치환 단계에서 시판 구입가능한 tert-부틸 4-아미노피페리딘-1-카르복실레이트를 사용하여 제조하였다. 에틸아민을 사용하는 우레아 형성에 따라, Boc-피페리딘 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 453.6.As shown in Scheme 1, a commercially available tert-butyl 4-aminopiperidine-1-carboxylate was prepared in the second nucleophilic aromatic substitution step. Following urea formation using ethylamine, the Boc-piperidine intermediate was treated with TFA to afford the title compound. (M + H) 453.6.

실시예 361: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(피페리딘-4-일아미노)-1,3,5-트리아진-2-일)페닐)-3-에틸우레아의 제조Example 361: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (piperidin-4-ylamino) -1,3, Preparation of 5-triazin-2-yl) phenyl) -3-ethylurea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 N1-(2-(디메틸아미노)에틸)-N1-메틸벤젠-1,4-디아민을 사용하여 제조하였다. (M+H) 614.3.As shown in Scheme 1, N1- (2- (dimethylamino) ethyl) -N1-methylbenzene-1,4-diamine was prepared in the urea formation step. (M + H) 614.3.

하기 화합물을 위해 필요한 벤젠-1,4-디아민 중간체를 반응식 4에 요약된 바와 같이 제조하였다.The necessary benzene-1,4-diamine intermediates for the following compounds were prepared as outlined in Scheme 4.

실시예 362: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(피페리딘-4-일아미노)-1,3,5-트리아진-2-일)페닐)-3-에틸우레아의 제조Example 362: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (piperidin-4-ylamino) -1,3, Preparation of 5-triazin-2-yl) phenyl) -3-ethylurea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 1-(4-아미노페닐)-N,N-디메틸피페리딘-4-아민을 사용하여 제조하였다. (M+H) 640.4.As shown in Scheme 1, 1- (4-aminophenyl) -N, N-dimethylpiperidin-4-amine was prepared in the urea formation step. (M + H) 640.4.

1-(4-아미노페닐)-N,N-디메틸피페리딘-4-아민의 제조:Preparation of 1- (4-aminophenyl) -N, N-dimethylpiperidin-4-amine:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 363: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(피페리딘-4-일아미노)-1,3,5-트리아진-2-일)페닐)-3-에틸우레아의 제조Example 363: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (piperidin-4-ylamino) -1,3, Preparation of 5-triazin-2-yl) phenyl) -3-ethylurea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 N1-(2-메톡시에틸)벤젠-1,4-디아민을 사용하여 제조하였다. (M+H) 587.3.As shown in Scheme 1, N1- (2-methoxyethyl) benzene-1,4-diamine was prepared in the urea formation step. (M + H) 587.3.

N1-(2-메톡시에틸)벤젠-1,4-디아민의 제조:Preparation of N1- (2-methoxyethyl) benzene-1,4-diamine:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 364: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(피페리딘-4-일아미노)-1,3,5-트리아진-2-일)페닐)-3-에틸우레아의 제조Example 364: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (piperidin-4-ylamino) -1,3, Preparation of 5-triazin-2-yl) phenyl) -3-ethylurea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 2-(4-아미노페닐아미노)에탄올을 사용하여 제조하였다. (M+H) 573.3.As shown in Scheme 1, it was prepared using 2- (4-aminophenylamino) ethanol in the urea formation step. (M + H) 573.3.

2-(4-아미노페닐아미노)에탄올의 제조:Preparation of 2- (4-aminophenylamino) ethanol:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 365: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(피페리딘-4-일아미노)-1,3,5-트리아진-2-일)페닐)-3-에틸우레아의 제조Example 365: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (piperidin-4-ylamino) -1,3, Preparation of 5-triazin-2-yl) phenyl) -3-ethylurea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 N1-(1-메틸피페리딘-4-일)벤젠-1,4-디아민을 사용하여 제조하였다. (M+H) 626.3.As shown in Scheme 1, N1- (1-methylpiperidin-4-yl) benzene-1,4-diamine was prepared in the urea forming step. (M + H) 626.3.

N1-(1-메틸피페리딘-4-일)벤젠-1,4-디아민의 제조:Preparation of N1- (1-methylpiperidin-4-yl) benzene-1,4-diamine:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 366: 1-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-일메틸)페닐)우레아의 제조Example 366: 1- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1,3,5-triazin-2-yl) phenyl Preparation of) -3- (4- (piperazin-1-ylmethyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노벤질)피페라진-1-카르복실레이트를 사용하여 제조하였다. 우레아 형성에 따라, Boc-피페리딘 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 612.3.As shown in Scheme 1, a commercially available tert-butyl 4- (4-aminobenzyl) piperazine-1-carboxylate was prepared in the urea forming step. Upon urea formation, the Boc-piperidine intermediate was treated with TFA to afford the title compound. (M + H) 612.3.

실시예 367: 1-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)-3-(4-((디메틸아미노)메틸)페닐)우레아의 제조Example 367: 1- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1,3,5-triazin-2-yl) phenyl Preparation of) -3- (4-((dimethylamino) methyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-((디메틸아미노)메틸)아닐린을 사용하여 제조하였다. (M+H) 571.3.As shown in Scheme 1, a commercially available 4-((dimethylamino) methyl) aniline was prepared in the urea forming step. (M + H) 571.3.

실시예 368: 1-(4-(아미노메틸)페닐)-3-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)우레아의 제조Example 368: 1- (4- (aminomethyl) phenyl) -3- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 tert-부틸 4-아미노벤질카르바메이트를 사용하여 제조하였다. 우레아 형성에 따라, Boc-아민 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 543.3.As shown in Scheme 1, a commercially available tert-butyl 4-aminobenzylcarbamate was prepared in the urea forming step. Upon urea formation, the Boc-amine intermediate was treated with TFA to afford the title compound. (M + H) 543.3.

실시예 369: 1-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(피롤리딘-1-일메틸)페닐)우레아의 제조Example 369: 1- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1,3,5-triazin-2-yl) phenyl Preparation of) -3- (4- (pyrrolidin-1-ylmethyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(피롤리딘-1-일메틸)아닐린을 사용하여 제조하였다. (M+H) 597.3.As shown in Scheme 1, it was prepared using commercially available 4- (pyrrolidin-1-ylmethyl) aniline in the urea forming step. (M + H) 597.3.

실시예 370: 1-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(4-메틸피페라진-1-일)에톡시)페닐)우레아의 제조Example 370: 1- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1,3,5-triazin-2-yl) phenyl Preparation of) -3- (4- (2- (4-methylpiperazin-1-yl) ethoxy) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(4-메틸피페라진-1-일)에톡시)아닐린을 사용하여 제조하였다. (M+H) 656.4.As shown in Scheme 1, it was prepared using 4- (2- (4-methylpiperazin-1-yl) ethoxy) aniline in the urea formation step. (M + H) 656.4.

하기 화합물을 위해 필요한 4-(알콕시)아닐린 중간체를 반응식 5에 요약된 바와 같이 제조하였다.The 4- (alkoxy) aniline intermediate required for the following compound was prepared as summarized in Scheme 5.

실시예 371: 1-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(피롤리딘-1-일)에톡시)페닐)우레아의 제조Example 371: 1- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1,3,5-triazin-2-yl) phenyl Preparation of) -3- (4- (2- (pyrrolidin-1-yl) ethoxy) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(피롤리딘-1-일)에톡시)아닐린을 사용하여 제조하였다. (M+H) 627.3.As shown in Scheme 1, it was prepared using 4- (2- (pyrrolidin-1-yl) ethoxy) aniline in the urea formation step. (M + H) 627.3.

4-(2-(피롤리딘-1-일)에톡시)아닐린의 제조:Preparation of 4- (2- (pyrrolidin-1-yl) ethoxy) aniline:

4-플루오로니트로벤젠 및 적절한 알콜로부터 반응식 5에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 5 from 4-fluoronitrobenzene and appropriate alcohol.

실시예 372: 1-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-히드록시에톡시)페닐)우레아의 제조Example 372: 1- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1,3,5-triazin-2-yl) phenyl Preparation of) -3- (4- (2-hydroxyethoxy) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 2-(4-아미노페녹시)에탄올을 사용하여 제조하였다. (M+H) 574.3.As shown in Scheme 1, it was prepared using 2- (4-aminophenoxy) ethanol in the urea formation step. (M + H) 574.3.

2-(4-아미노페녹시)에탄올의 제조:Preparation of 2- (4-aminophenoxy) ethanol:

4-플루오로니트로벤젠 및 적절한 알콜로부터 반응식 5에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 5 from 4-fluoronitrobenzene and appropriate alcohol.

실시예 373: N-(4-(3-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)우레이도)페닐)-2-(디메틸아미노)아세트아미드의 제조Example 373: N- (4- (3- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1,3,5-triazine Preparation of -2-yl) phenyl) ureido) phenyl) -2- (dimethylamino) acetamide

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 N-(4-아미노페닐)-2-(디메틸아미노)아세트아미드를 사용하여 제조하였다. (M+H) 614.3.As shown in Scheme 1, a commercially available N- (4-aminophenyl) -2- (dimethylamino) acetamide was prepared in the urea forming step. (M + H) 614.3.

실시예 374: N-(4-(3-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)우레이도)페닐)-2-(4-메틸피페라진-1-일)아세트아미드의 제조Example 374: N- (4- (3- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1,3,5-triazine Preparation of -2-yl) phenyl) ureido) phenyl) -2- (4-methylpiperazin-1-yl) acetamide

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 N-(4-아미노페닐)-2-(4-메틸피페라진-1-일)아세트아미드를 사용하여 제조하였다. (M+H) 669.4.As shown in Scheme 1, a commercially available N- (4-aminophenyl) -2- (4-methylpiperazin-1-yl) acetamide was prepared in the urea forming step. (M + H) 669.4.

실시예 375: N-(4-(3-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)우레이도)페닐)-2-(피롤리딘-1-일)아세트아미드의 제조Example 375 N- (4- (3- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -1,3,5-triazine Preparation of -2-yl) phenyl) ureido) phenyl) -2- (pyrrolidin-1-yl) acetamide

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 N-(4-아미노페닐)-2-(피롤리딘-1-일)아세트아미드를 사용하여 제조하였다. (M+H) 640.3.As shown in Scheme 1, a commercially available N- (4-aminophenyl) -2- (pyrrolidin-1-yl) acetamide was prepared in the urea forming step. (M + H) 640.3.

실시예 376: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아의 제조Example 376: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (pyridin-3-yl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-3-아민을 사용하여 제조하였다. (M+H) 461.2.As shown in Scheme 1, a commercially available pyridin-3-amine was prepared in the urea forming step. (M + H) 461.2.

실시예 377: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조Example 377 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (pyridin-4-yl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-4-아민을 사용하여 제조하였다. (M+H) 461.2.As shown in Scheme 1, a commercially available pyridin-4-amine was prepared in the urea forming step. (M + H) 461.2.

실시예 378: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조Example 378: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-메틸피페라진-1-일)아닐린을 사용하여 제조하였다. (M+H) 558.3.As shown in Scheme 1, a commercially available 4- (4-methylpiperazin-1-yl) aniline was prepared in the urea forming step. (M + H) 558.3.

실시예 379: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-((4-메틸피페라진-1-일)메틸)페닐)우레아의 제조Example 379: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4-((4-methylpiperazin-1-yl) methyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-((4-메틸피페라진-1-일)메틸)아닐린을 사용하여 제조하였다. (M+H) 572.3.As shown in Scheme 1, a commercially available 4-((4-methylpiperazin-1-yl) methyl) aniline was prepared in the urea forming step. (M + H) 572.3.

실시예 380: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-일메틸)페닐)우레아의 제조Example 380: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4- (piperazin-1-ylmethyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노벤질)피페라진-1-카르복실레이트를 사용하여 제조하였다. 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 558.3.As shown in Scheme 1, a commercially available tert-butyl 4- (4-aminobenzyl) piperazine-1-carboxylate was prepared in the urea forming step. Upon urea formation, the Boc-piperazine intermediate was treated with TFA to afford the title compound. (M + H) 558.3.

실시예 381: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-((디메틸아미노)메틸)페닐)우레아의 제조Example 381: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4-((dimethylamino) methyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-((디메틸아미노)메틸)아닐린를 사용하여 제조하였다. (M+H) 517.3.As shown in Scheme 1, a commercially available 4-((dimethylamino) methyl) aniline was prepared in the urea forming step. (M + H) 517.3.

실시예 382: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(아미노메틸)페닐)우레아의 제조Example 382: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4- (aminomethyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 tert-부틸 4-아미노벤질카르바메이트를 사용하여 제조하였다. 우레아 형성에 따라, Boc-아민 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 489.3.As shown in Scheme 1, a commercially available tert-butyl 4-aminobenzylcarbamate was prepared in the urea forming step. Upon urea formation, the Boc-amine intermediate was treated with TFA to afford the title compound. (M + H) 489.3.

실시예 383: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피롤리딘-1-일메틸)페닐)우레아의 제조Example 383: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4- (pyrrolidin-1-ylmethyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(피롤리딘-1-일메틸)아닐린을 사용하여 제조하였다. (M+H) 543.3.As shown in Scheme 1, it was prepared using commercially available 4- (pyrrolidin-1-ylmethyl) aniline in the urea forming step. (M + H) 543.3.

실시예 384: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(피롤리딘-1-일)에톡시)페닐)우레아의 제조Example 384 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4- (2- (pyrrolidin-1-yl) ethoxy) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(피롤리딘-1-일)에톡시)아닐린을 사용하여 제조하였다. (M+H) 573.3.As shown in Scheme 1, it was prepared using 4- (2- (pyrrolidin-1-yl) ethoxy) aniline in the urea formation step. (M + H) 573.3.

실시예 385: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)에톡시)페닐)우레아의 제조Example 385 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4- (2- (dimethylamino) ethoxy) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(디메틸아미노)에톡시)아닐린을 사용하여 제조하였다. (M+H) 547.3.As shown in Scheme 1, it was prepared using 4- (2- (dimethylamino) ethoxy) aniline in the urea formation step. (M + H) 547.3.

4-(2-(디메틸아미노)에톡시)아닐린의 제조:Preparation of 4- (2- (dimethylamino) ethoxy) aniline:

4-플루오로니트로벤젠 및 적절한 알콜로부터 반응식 5에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 5 from 4-fluoronitrobenzene and appropriate alcohol.

실시예 386: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-일)피리딘-3-일)우레아의 제조Example 386 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (6- (4-methylpiperazin-1-yl) pyridin-3-yl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 5-(4-메틸피페라진-1-일)피리딘-2-아민을 사용하여 제조하였다. (M+H) 559.3.As shown in Scheme 1, a commercially available 5- (4-methylpiperazin-1-yl) pyridin-2-amine was prepared in the urea forming step. (M + H) 559.3.

실시예 387: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-일)페닐)우레아의 제조Example 387: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4- (piperazin-1-yl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노페닐)피페라진-1-카르복실레이트를 사용하여 제조하였다. 우레아 형성에 따라, Boc-아민 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. (M+H) 544.3.As shown in Scheme 1, a commercially available tert-butyl 4- (4-aminophenyl) piperazine-1-carboxylate was prepared in the urea forming step. Upon urea formation, the Boc-amine intermediate was treated with TFA to afford the title compound. (M + H) 544.3.

실시예 388: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)우레아의 제조Example 388: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropylamino) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 1-(4-아미노페닐)-N,N-디메틸피페리딘-4-아민을 사용하여 제조하였다. (M+H) 586.4.As shown in Scheme 1, 1- (4-aminophenyl) -N, N-dimethylpiperidin-4-amine was prepared in the urea formation step. (M + H) 586.4.

실시예 389: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필(메틸)아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조Example 389: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropyl (methyl) amino) -1,3,5- Preparation of triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-메틸피페라진-1-일)아닐린을 사용하여 제조하였다. (M+H) 572.3.As shown in Scheme 1, a commercially available 4- (4-methylpiperazin-1-yl) aniline was prepared in the urea forming step. (M + H) 572.3.

실시예 390: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필(메틸)아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-((디메틸아미노)메틸)페닐)우레아의 제조Example 390: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropyl (methyl) amino) -1,3,5- Preparation of triazin-2-yl) phenyl) -3- (4-((dimethylamino) methyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-((디메틸아미노)메틸)아닐린을 사용하여 제조하였다. (M+H) 531.3.As shown in Scheme 1, a commercially available 4-((dimethylamino) methyl) aniline was prepared in the urea forming step. (M + H) 531.3.

실시예 391: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(이소프로필(메틸)아미노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)에톡시)페닐)우레아의 제조Example 391: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (isopropyl (methyl) amino) -1,3,5- Preparation of triazin-2-yl) phenyl) -3- (4- (2- (dimethylamino) ethoxy) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(디메틸아미노)에톡시)아닐린을 사용하여 제조하였다. (M+H) 561.3.As shown in Scheme 1, it was prepared using 4- (2- (dimethylamino) ethoxy) aniline in the urea formation step. (M + H) 561.3.

실시예 392: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아의 제조 (반응식 6).Example 392 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-thiomorpholino-1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (pyridin-3-yl) urea (Scheme 6).

단계 1: 8-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄의 제조:Step 1: Preparation of 8- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2.1] octane:

아세톤 (20 mL) 및 빙수 (20 mL) 중 2,4-디클로로-6-(4-니트로페닐)-1,3,5-트리아진 (1.25 g, 4.61 mmol)의 용액을 제조하였다. 여기에 아세톤 (15 mL) 및 물 (15 mL) 중 3-옥사-8-아자비시클로[3.2.1]옥탄-히드로클로라이드 (0.655 g, 4.38 mmol) 및 중탄산나트륨 (0.775 g, 9.22 mmol)의 현탁액을 10 분에 걸쳐 적가하였다. 생성된 황갈색 용액을 0℃에서 2 시간 동안 교반시킨 후에, 18 시간에 걸쳐 점차 실온으로 가온시켰다. 밝은 갈색 현탁액을 여과하고, 물로 세척하였다. 조 생성물을 메틸렌 클로라이드 중 0-1.5％ 메탄올로 용리하는 실리카겔 컬럼 크로마토그래피로 정제하여 8-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.89 g, 56％)을 회백색 고체로서 수득하였다. (M+H) 348.1.A solution of 2,4-dichloro-6- (4-nitrophenyl) -1,3,5-triazine (1.25 g, 4.61 mmol) in acetone (20 mL) and ice water (20 mL) was prepared. Here suspension of 3-oxa-8-azabicyclo [3.2.1] octane-hydrochloride (0.655 g, 4.38 mmol) and sodium bicarbonate (0.775 g, 9.22 mmol) in acetone (15 mL) and water (15 mL) Was added dropwise over 10 minutes. The resulting tan solution was stirred at 0 ° C. for 2 hours and then gradually warmed to room temperature over 18 hours. The light brown suspension was filtered and washed with water. The crude product was purified by silica gel column chromatography eluting with 0-1.5% methanol in methylene chloride to give 8- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) 3-Oxa-8-azabicyclo [3.2.1] octane (0.89 g, 56%) was obtained as off-white solid. (M + H) 348.1.

단계 2: 8-(4-(4-니트로페닐)-6-티오모르폴리노-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄의 제조:Step 2: 8- (4- (4-nitrophenyl) -6-thiomorpholino-1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2.1] octane Manufacture of:

아세톤 (5 mL) 및 물 (10 mL) 중 8-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.450 g, 1.29 mmol)의 용액을 제조하였다. 여기에 탄산나트륨 (0.274 g, 2.59 mmol)에 이어 티오모르폴린 (0.134 ml, 1.42 mmol)을 첨가하였다. 생성된 밝은 황갈샐 현탁액을 60℃에서 2.5 시간 동안 교반되도록 하였다. 현탁액을 여과하고, 고체를 물로 세척하고, 진공하에 건조시켜 8-(4-(4-니트로페닐)-6-티오모르폴리노-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.455 g, 85％)을 백색 고체로서 수득하였다.8- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo in acetone (5 mL) and water (10 mL) A solution of [3.2.1] octane (0.450 g, 1.29 mmol) was prepared. To this was added sodium carbonate (0.274 g, 2.59 mmol) followed by thiomorpholine (0.134 ml, 1.42 mmol). The resulting bright yellow brown suspension was allowed to stir at 60 ° C. for 2.5 hours. The suspension is filtered, the solid is washed with water and dried under vacuum to afford 8- (4- (4-nitrophenyl) -6-thiomorpholino-1,3,5-triazin-2-yl) -3- Oxa-8-azabicyclo [3.2.1] octane (0.455 g, 85%) was obtained as a white solid.

Figure 112010076169004-pct00068
Figure 112010076169004-pct00068

단계 3: 4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)아닐린의 제조:Step 3: 4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-thiomorpholino-1,3,5-triazin-2-yl) aniline Manufacture of:

피리딘 (3 ml) 및 DMF (6 ml) 중 8-(4-(4-니트로페닐)-6-티오모르폴리노-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.418 g, 1.01 mmol)의 현탁액을 제조하였다. 이어서, 주석(II) 클로라이드 이수화물 (0.569 g, 2.52 mmol)을 첨가하고, 회백색 현탁액을 실온에서 16 시간 동안 교반되도록 하고, 이 시점에 현탁액은 밝은 황색이었다. 현탁액을 여과하고, 메탄올로 세척하고, 농축시켰다. LCMS는 반응이 완결되지 않았음을 나타냈다. 조 생성물을 DMF (6 ml) 및 피리딘 (3 ml) 중에 용해시키고, 추가의 주석(II) 클로라이드 이수화물 (0.569 g, 2.52 mmol)을 첨가하였다. 용액을 실온에서 18 시간 동안 교반한 후에 여과하였다. 침전물을 메탄올로 세척하고, 여과물을 농축시켜 4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)아닐린 (0.195 g, 50％)을 황색 고체로서 수득하였다. (M+H) 385.1.8- (4- (4-nitrophenyl) -6-thiomorpholino-1,3,5-triazin-2-yl) -3-oxa-8 in pyridine (3 ml) and DMF (6 ml) A suspension of azabicyclo [3.2.1] octane (0.418 g, 1.01 mmol) was prepared. Tin (II) chloride dihydrate (0.569 g, 2.52 mmol) was then added and the off-white suspension was allowed to stir at room temperature for 16 hours, at which point the suspension was bright yellow. The suspension is filtered, washed with methanol and concentrated. LCMS indicated that the reaction was not complete. The crude product was dissolved in DMF (6 ml) and pyridine (3 ml) and additional tin (II) chloride dihydrate (0.569 g, 2.52 mmol) was added. The solution was stirred at rt for 18 h and then filtered. The precipitate was washed with methanol and the filtrate was concentrated to give 4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-thiomorpholino-1,3,5 -Triazin-2-yl) aniline (0.195 g, 50%) was obtained as a yellow solid. (M + H) 385.1.

단계 4: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아의 제조:Step 4: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-thiomorpholino-1,3,5-triazine-2- Preparation of yl) phenyl) -3- (pyridin-3-yl) urea:

반응식 1에 기재된, 메틸렌 클로라이드 중 트리포스겐 및 트리에틸아민을 사용하는 우레아 형성 방법은 시판 구입가능한 피리딘-3-아민을 아민 성분으로서 사용하여 활용하였다. HPLC (20 분에 걸쳐 물 중 5-95％ 아세토니트릴, 0.05％ TFA 완충액, 워터스 아틀란티스 컬럼)로 정제하여 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아 (0.032 g, 63％)를 회백색 고체로서 수득하였다. (M+H) 505.2.The urea formation method using triphosgene and triethylamine in methylene chloride, described in Scheme 1, was utilized using commercially available pyridin-3-amine as the amine component. Purification by HPLC (5-95% acetonitrile in water, 0.05% TFA buffer, Waters Atlantis column over 20 minutes) to 1- (4- (4- (3- (oxa-8-azabicyclo [3.2.1] octane) -8-yl) -6-thiomorpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridin-3-yl) urea (0.032 g, 63%) as off-white solid Obtained. (M + H) 505.2.

실시예 393: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조Example 393: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-thiomorpholino-1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (pyridin-4-yl) urea

반응식 6에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-4-아민을 사용하여 제조하였다. 수율; 28 mg (54％); (M+H) 505.2.As shown in Scheme 6, a commercially available pyridin-4-amine was prepared in the urea forming step. yield; 28 mg (54%); (M + H) 505.2.

실시예 394: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조Example 394: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-thiomorpholino-1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea

반응식 6에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-메틸피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 44 mg (73％); (M+H) 602.3.As shown in Scheme 6, a commercially available 4- (4-methylpiperazin-1-yl) aniline was prepared in the urea forming step. yield; 44 mg (73%); (M + H) 602.3.

실시예 395: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-((디메틸아미노)메틸)페닐)우레아의 제조Example 395 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-thiomorpholino-1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (4-((dimethylamino) methyl) phenyl) urea

반응식 6에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-((디메틸아미노)메틸)아닐린을 사용하여 제조하였다. 수율; 19 mg (34％); (M+H) 561.3.As shown in Scheme 6, a commercially available 4-((dimethylamino) methyl) aniline was prepared in the urea forming step. yield; 19 mg (34%); (M + H) 561.3.

실시예 365: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)에톡시)페닐)우레아의 제조Example 365: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-thiomorpholino-1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (4- (2- (dimethylamino) ethoxy) phenyl) urea

반응식 6에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(디메틸아미노)에톡시)아닐린을 사용하여 제조하였다. 수율; 35 mg (59％); (M+H) 591.3.As shown in Scheme 6, it was prepared using 4- (2- (dimethylamino) ethoxy) aniline in the urea formation step. yield; 35 mg (59%); (M + H) 591.3.

실시예 397: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조Example 397 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (pyridine-4 Preparation of urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-4-아민을 사용하여 제조하였다. 수율; 44 mg (75％); (M+H) 491.2.As shown in Scheme 1, a commercially available pyridin-4-amine was prepared in the urea forming step. yield; 44 mg (75%); (M + H) 491.2.

실시예 398: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아의 제조Example 398: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (pyridine-3 Preparation of urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-3-아민을 사용하여 제조하였다. 수율; 46 mg (79％); (M+H) 491.2.As shown in Scheme 1, a commercially available pyridin-3-amine was prepared in the urea forming step. yield; 46 mg (79%); (M + H) 491.2.

실시예 399: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조Example 399: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of 4-methylpiperazin-1-yl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-((디메틸아미노)메틸)아닐린을 사용하여 제조하였다. 수율; 57 mg (81％); (M+H) 588.3.As shown in Scheme 1, a commercially available 4-((dimethylamino) methyl) aniline was prepared in the urea forming step. yield; 57 mg (81%); (M + H) 588.3.

실시예 400: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-일)피리딘-3-일)우레아의 제조Example 400: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (6- ( Preparation of 4-methylpiperazin-1-yl) pyridin-3-yl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 5-(4-메틸피페라진-1-일)피리딘-2-아민을 사용하여 제조하였다. 수율; 56 mg (79％); (M+H) 589.3.As shown in Scheme 1, a commercially available 5- (4-methylpiperazin-1-yl) pyridin-2-amine was prepared in the urea forming step. yield; 56 mg (79%); (M + H) 589.3.

실시예 401: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-((디메틸아미노)메틸)페닐)우레아의 제조Example 401: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of (dimethylamino) methyl) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-((디메틸아미노)메틸)아닐린을 사용하여 제조하였다. 수율; 28 mg (43％); (M+H) 547.3.As shown in Scheme 1, a commercially available 4-((dimethylamino) methyl) aniline was prepared in the urea forming step. yield; 28 mg (43%); (M + H) 547.3.

실시예 402: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)에톡시)페닐)우레아의 제조Example 402: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of 2- (dimethylamino) ethoxy) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(디메틸아미노)에톡시)아닐린을 사용하여 제조하였다. 수율; 50 mg (72％); (M+H) 577.3.As shown in Scheme 1, it was prepared using 4- (2- (dimethylamino) ethoxy) aniline in the urea formation step. yield; 50 mg (72%); (M + H) 577.3.

실시예 403: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(피롤리딘-1-일)에톡시)페닐)우레아의 제조Example 403: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of 2- (pyrrolidin-1-yl) ethoxy) phenyl) urea

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(피롤리딘-1-일)에톡시)아닐린을 사용하여 제조하였다. 수율; 41 mg (57％); (M+H) 603.3.As shown in Scheme 1, it was prepared using 4- (2- (pyrrolidin-1-yl) ethoxy) aniline in the urea formation step. yield; 41 mg (57%); (M + H) 603.3.

실시예 404: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(3,6-디히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조 (반응식 7)Example 404: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (3,6-dihydro-2H-pyran-4-yl Preparation of) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea (Scheme 7)

단계 1: 8-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄의 제조: 실시예 392, 단계 1에 기재된 반응식 6에 나타낸 바와 같이, 제조하였다.Step 1: Preparation of 8- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2.1] octane: Example 392, as shown in Scheme 6 described in Step 1, was prepared.

단계 2: 8-(4-(3,6-디히드로-2H-피란-4-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄의 제조:Step 2: 8- (4- (3,6-dihydro-2H-pyran-4-yl) -6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3- Preparation of oxa-8-azabicyclo [3.2.1] octane:

마이크로파 바이알을 8-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.440 g, 1.27 mmol)으로 충전시켰다. 이어서, 톨루엔 (6 mL)을 첨가하고, 용액을 10 분 동안 질소로 살포하였다. 테트라키스(트리페닐포스핀)팔라듐(0) (0.088 g, 0.076 mmol) 및 트리부틸(3,6-디히드로-2H-피란-4-일)스탄난 (0.567 g, 1.52 mmol)을 첨가하였다. 바이알을 밀봉하고, 40 분 동안 마이크로파를 통해 100℃로 가열하였다. 추가의 트리부틸(3,6-디히드로-2H-피란-4-일)스탄난 (0.283 g, 0.76 mmol) 및 테트라키스(트리페닐포스핀)팔라듐(0) (0.022 g, 0.019 mmol)을 첨가하고, 현탁액을 마이크로파에 의해 추가 90 분 동안 110℃로 가열하였다. 이어서, 현탁액을 실온으로 냉각시키고, 셀라이트™를 통해 여과하였다. 필터 케이크를 에틸 아세테이트로 세척하고, 여과물을 감압하에 농축시켰다. 조 생성물을 메틸렌 클로라이드 중 0-2％ 메탄올로 용리하는 실리카겔 크로마토그래피로 정제하여 8-(4-(3,6-디히드로-2H-피란-4-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.430 g, 86％)을 밝은 황색 고체로서 수득하였다.

Figure 112010076169004-pct00069
Microwave vials were added to 8- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2.1] octane (0.440 g , 1.27 mmol). Toluene (6 mL) was then added and the solution sparged with nitrogen for 10 minutes. Tetrakis (triphenylphosphine) palladium (0) (0.088 g, 0.076 mmol) and tributyl (3,6-dihydro-2H-pyran-4-yl) stannan (0.567 g, 1.52 mmol) were added. . The vial was sealed and heated to 100 ° C. via microwave for 40 minutes. Additional tributyl (3,6-dihydro-2H-pyran-4-yl) stannan (0.283 g, 0.76 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.022 g, 0.019 mmol) Was added and the suspension was heated by microwave to 110 ° C. for an additional 90 minutes. The suspension was then cooled to room temperature and filtered through Celite ™. The filter cake was washed with ethyl acetate and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with 0-2% methanol in methylene chloride to give 8- (4- (3,6-dihydro-2H-pyran-4-yl) -6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2.1] octane (0.430 g, 86%) was obtained as a light yellow solid.
Figure 112010076169004-pct00069

단계 3: 4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(3,6-디히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)아닐린의 제조:Step 3: 4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (3,6-dihydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) aniline:

아세트산 (2 ml) 중 철 분말 (0.071 g, 1.27 mmol)의 혼합물을 15 분 동안 55℃로 가열하였다. 이어서, 물 (2 ml)을 첨가하고, 오일조를 껐다. 이어서, 에틸 아세테이트 (2 ml) 중 8-(4-(3,6-디히드로-2H-피란-4-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.100 g, 0.253 mmol)의 용액을 상기 따뜻한 용액에 5 분에 걸쳐 첨가하였다. 혼합물을 실온으로 냉각시키고, 16 시간 동안 교반되도록 하였다. 혼합물을 포화 수성 탄산나트륨을 함유한 분별 깔때기 내 경사분리 (4X)에 의해 에틸 아세테이트로 추출하였다. 합한 유기 추출물을 물, 염수로 세척하고, 건조시키고, 농축시켜 4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(3,6-디히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)아닐린 (0.068 g, 74％)을 수득하고, 이것을 다음 단계에서 정제 없이 사용하였다. (M+H) 366.4.A mixture of iron powder (0.071 g, 1.27 mmol) in acetic acid (2 ml) was heated to 55 ° C. for 15 minutes. Then water (2 ml) was added and the oil bath was turned off. Then 8- (4- (3,6-dihydro-2H-pyran-4-yl) -6- (4-nitrophenyl) -1,3,5-triazine-2 in ethyl acetate (2 ml) A solution of -yl) -3-oxa-8-azabicyclo [3.2.1] octane (0.100 g, 0.253 mmol) was added to the warm solution over 5 minutes. The mixture was cooled to rt and allowed to stir for 16 h. The mixture was extracted with ethyl acetate by decantation (4 ×) in a separatory funnel containing saturated aqueous sodium carbonate. The combined organic extracts were washed with water, brine, dried and concentrated to 4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (3,6-di Hydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) aniline (0.068 g, 74%) was obtained, which was used without purification in the next step. (M + H) 366.4.

단계 4: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(3,6-디히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조:Step 4: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (3,6-dihydro-2H-pyran-4-yl) Preparation of -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea:

반응식 1에 기재된, 메틸렌 클로라이드 중 트리포스겐 및 트리에틸아민을 사용하는 우레아 형성 방법은 시판 구입가능한 피리딘-4-아민을 아민 성분으로서 사용하여 활용하였다. HPLC (20 분에 걸쳐 물 중 5-95％ 아세토니트릴, 0.05％ TFA 완충액, 워터스 아틀란티스 컬럼)로 정제하여 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(3,6-디히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아 (0.034 g, 75％)를 밝은 황색 고체로서 수득하였다. (M+H) 486.2.The urea formation method using triphosgene and triethylamine in methylene chloride, described in Scheme 1, was utilized using commercially available pyridin-4-amine as the amine component. Purification by HPLC (5-95% acetonitrile in water, 0.05% TFA buffer, Waters Atlantis column over 20 minutes) to 1- (4- (4- (3- (oxa-8-azabicyclo [3.2.1] octane) -8-yl) -6- (3,6-dihydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) Urea (0.034 g, 75%) was obtained as a light yellow solid. (M + H) 486.2.

실시예 405: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(3,6-디히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조:Example 405: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (3,6-dihydro-2H-pyran-4-yl Preparation of) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-메틸피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 44 mg (82％); (M+H) 583.3.As shown in Scheme 7, it was prepared using commercially available 4- (4-methylpiperazin-1-yl) aniline in the urea forming step. yield; 44 mg (82%); (M + H) 583.3.

실시예 406: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조:Example 406: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea:

반응식 7; 하기 기재된 대표적인 합성에 나타낸 바와 같이 제조하였다.Scheme 7; Prepared as shown in the representative synthesis described below.

4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)아닐린의 제조:4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine- Preparation of 2-yl) aniline:

에틸 아세테이트 (5 ml), 메탄올 (5 ml) 및 메틸렌 클로라이드 (2 ml - EA/메탄올 중 SM의 불량한 용해도 때문에 첨가함) 중 8-(4-(3,6-디히드로-2H-피란-4-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (실시예 DJR-51, 단계 2에 기재된 바와 같이 제조함) (0.260 g, 0.658 mmol)의 용액을 제조하고, 10％ 탄소상 팔라듐 (0.078 g, 30 중량％)을 첨가하였다. 플라스크를 수소 기체 (풍선)로 퍼징시키고, 수소 양압 하에서 16 시간 동안 교반되도록 하였다. 추가의 탄소상 팔라듐 (0.039 g)을 첨가하고, 현탁액을 수소 기체 (풍선)로 퍼징시키고, 추가 3 시간 동안 교반하였다. 플라스크를 수소 기체로 퍼징시키고, 추가 1 시간 동안 교반하였다. 현탁액을 셀라이트™를 통해 여과하고, 필터 케이크를 에틸 아세테이트로 세척하고, 여과물을 농축시켜 4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)아닐린 (0.220 g, 91％)을 회백색 고체로서 수득하였다. HRMS 368.2080 (M+H, 계산치), 368.2085 (M+H, 관측치).Ethyl acetate (5 ml), methanol (5 ml) and methylene chloride (2 ml-added because of poor solubility of SM in EA / methanol) in 8- (4- (3,6-dihydro-2H-pyran-4) -Yl) -6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2.1] octane (Example DJR-51, step 2 (0.260 g, 0.658 mmol) was prepared and 10% palladium on carbon (0.078 g, 30% by weight) was added. The flask was purged with hydrogen gas (balloon) and allowed to stir for 16 hours under positive hydrogen pressure. Additional palladium on carbon (0.039 g) was added and the suspension was purged with hydrogen gas (balloon) and stirred for an additional 3 hours. The flask was purged with hydrogen gas and stirred for an additional 1 hour. The suspension is filtered through Celite ™, the filter cake is washed with ethyl acetate and the filtrate is concentrated to 4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl)- 6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) aniline (0.220 g, 91%) was obtained as off-white solid. HRMS 368.2080 (M + H, calculated), 368.2085 (M + H, observed).

1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조:1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5- Preparation of Triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea:

반응식 1에 기재된, 메틸렌 클로라이드 중 트리포스겐 및 트리에틸아민을 사용하는 우레아 형성 방법은 시판 구입가능한 피리딘-4-아민을 아민 성분으로서 사용하여 활용하였다. HPLC (20 분에 걸쳐 물 중 5-95％ 아세토니트릴, 0.05％ TFA 완충액, 워터스 아틀란티스 컬럼)로 정제하여 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아 (0.0461 g, 82％)를 회백색 고체로서 수득하였다. (M+H) 488.2.The urea formation method using triphosgene and triethylamine in methylene chloride, described in Scheme 1, was utilized using commercially available pyridin-4-amine as the amine component. Purification by HPLC (5-95% acetonitrile in water, 0.05% TFA buffer, Waters Atlantis column over 20 minutes) to 1- (4- (4- (3- (oxa-8-azabicyclo [3.2.1] octane) -8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea (0.0461 g , 82%) was obtained as an off-white solid. (M + H) 488.2.

실시예 407: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조:Example 407: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-메틸피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 54 mg (79％); (M+H) 585.3.As shown in Scheme 7, it was prepared using commercially available 4- (4-methylpiperazin-1-yl) aniline in the urea forming step. yield; 54 mg (79%); (M + H) 585.3.

실시예 408: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)에톡시)페닐)우레아의 제조:Example 408: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (2- (dimethylamino) ethoxy) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(디메틸아미노)에톡시)아닐린을 사용하여 제조하였다. 수율; 49 mg (73％); (M+H) 572.3.As shown in Scheme 7, it was prepared using 4- (2- (dimethylamino) ethoxy) aniline in the urea formation step. yield; 49 mg (73%); (M + H) 572.3.

실시예 409: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-((디메틸아미노)메틸)페닐)우레아의 제조:Example 409: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4-((dimethylamino) methyl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-((디메틸아미노)메틸)아닐린을 사용하여 제조하였다. 수율; 21 mg (33％); (M+H) 544.3.As shown in Scheme 7, it was prepared using commercially available 4-((dimethylamino) methyl) aniline in the urea forming step. yield; 21 mg (33%); (M + H) 544.3.

실시예 410: 1-(4-(4-((1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵탄-5-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조:Example 410: 1- (4- (4-((1S, 4S) -2-oxa-5-azabicyclo [2.2.1] heptan-5-yl) -6-((R) -3-methylmor Preparation of Polyno) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-4-아민을 사용하여 제조하였다. 수율; 45 mg (70％); (M+H) 489.2.As shown in Scheme 1, a commercially available pyridin-4-amine was prepared in the urea forming step. yield; 45 mg (70%); (M + H) 489.2.

실시예 411: 1-(4-(4-((1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵탄-5-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아의 제조:Example 411 1- (4- (4-((1S, 4S) -2-oxa-5-azabicyclo [2.2.1] heptan-5-yl) -6-((R) -3-methylmor Preparation of Polyno) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-3-yl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-3-아민을 사용하여 제조하였다. 수율; 60 mg (95％); (M+H) 489.2.As shown in Scheme 1, a commercially available pyridin-3-amine was prepared in the urea forming step. yield; 60 mg (95%); (M + H) 489.2.

실시예 412: 1-(4-(4-((1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵탄-5-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조:Example 412: 1- (4- (4-((1S, 4S) -2-oxa-5-azabicyclo [2.2.1] heptan-5-yl) -6-((R) -3-methylmor Preparation of Polyno) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-메틸피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 69 mg (90％); (M+H) 586.3.As shown in Scheme 1, a commercially available 4- (4-methylpiperazin-1-yl) aniline was prepared in the urea forming step. yield; 69 mg (90%); (M + H) 586.3.

실시예 413: 1-(4-(4-((1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵탄-5-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-((4-메틸피페라진-1-일)메틸)페닐)우레아의 제조:Example 413: 1- (4- (4-((1S, 4S) -2-oxa-5-azabicyclo [2.2.1] heptan-5-yl) -6-((R) -3-methylmor Preparation of Polyno) -1,3,5-triazin-2-yl) phenyl) -3- (4-((4-methylpiperazin-1-yl) methyl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-((4-메틸피페라진-1-일)메틸)아닐린을 사용하여 제조하였다. 수율; 73 mg (94％); (M+H) 600.3.As shown in Scheme 1, a commercially available 4-((4-methylpiperazin-1-yl) methyl) aniline was prepared in the urea forming step. yield; 73 mg (94%); (M + H) 600.3.

실시예 414: 1-(4-(4-((1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵탄-5-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피롤리딘-1-일메틸)페닐)우레아의 제조:Example 414: 1- (4- (4-((1S, 4S) -2-oxa-5-azabicyclo [2.2.1] heptan-5-yl) -6-((R) -3-methylmor Preparation of Polyno) -1,3,5-triazin-2-yl) phenyl) -3- (4- (pyrrolidin-1-ylmethyl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(피롤리딘-1-일메틸)아닐린을 사용하여 제조하였다. 수율; 56 mg (75％); (M+H) 571.3.As shown in Scheme 1, it was prepared using commercially available 4- (pyrrolidin-1-ylmethyl) aniline in the urea forming step. yield; 56 mg (75%); (M + H) 571.3.

실시예 415: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아의 제조:Example 415: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (pyridin-3-yl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-3-아민을 사용하여 제조하였다. 수율; 44 mg (66％); (M+H) 503.2.As shown in Scheme 1, a commercially available pyridin-3-amine was prepared in the urea forming step. yield; 44 mg (66%); (M + H) 503.2.

실시예 416: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아의 제조:Example 416: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-4-아민을 사용하여 제조하였다. 수율; 35 mg (53％); (M+H) 503.2.As shown in Scheme 1, a commercially available pyridin-4-amine was prepared in the urea forming step. yield; 35 mg (53%); (M + H) 503.2.

실시예 417: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조:Example 417: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-메틸피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 58 mg (62％); (M+H) 600.3.As shown in Scheme 1, a commercially available 4- (4-methylpiperazin-1-yl) aniline was prepared in the urea forming step. yield; 58 mg (62%); (M + H) 600.3.

실시예 418: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피롤리딘-1-일메틸)페닐)우레아의 제조:Example 418: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (pyrrolidin-1-ylmethyl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(피롤리딘-1-일메틸)아닐린을 사용하여 제조하였다. 수율; 41 mg (45％); (M+H) 585.5.As shown in Scheme 1, it was prepared using commercially available 4- (pyrrolidin-1-ylmethyl) aniline in the urea forming step. yield; 41 mg (45%); (M + H) 585.5.

실시예 419: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)에톡시)페닐)우레아의 제조:Example 419: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (2- (dimethylamino) ethoxy) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(디메틸아미노)에톡시)아닐린을 사용하여 제조하였다. 수율; 43 mg (47％); (M+H) 589.3.As shown in Scheme 1, it was prepared using 4- (2- (dimethylamino) ethoxy) aniline in the urea formation step. yield; 43 mg (47%); (M + H) 589.3.

실시예 420: (R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아의 제조:Example 420: (R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (pyridin-3-yl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 피리딘-3-아민을 사용하여 제조하였다. 수율; 45 mg (77％); (M+H) 476.2.As shown in Scheme 7, a commercially available pyridin-3-amine was prepared in the urea forming step. yield; 45 mg (77%); (M + H) 476.2.

실시예 421: (R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조:Example 421: (R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-메틸피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 53 mg (75％); (M+H) 573.3.As shown in Scheme 7, it was prepared using commercially available 4- (4-methylpiperazin-1-yl) aniline in the urea forming step. yield; 53 mg (75%); (M + H) 573.3.

실시예 422: (R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-일)페닐)우레아의 제조:Example 422: (R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (4- (piperazin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 tert-부틸 4-(4-아미노페닐)피페라진-1-카르복실레이트를 사용하여 제조하였다. 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. 수율; 63 mg (90％); (M+H) 559.3.As shown in Scheme 7, it was prepared using commercially available tert-butyl 4- (4-aminophenyl) piperazine-1-carboxylate in the urea forming step. Upon urea formation, the Boc-piperazine intermediate was treated with TFA to afford the title compound. yield; 63 mg (90%); (M + H) 559.3.

실시예 423: 1-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-((S)-3-메틸피페라진-1-일)페닐)우레아의 제조:Example 423 1- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (4-((S) -3-methylpiperazin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 (S)-tert-부틸 4-(4-아미노페닐)-3-메틸피페라진-1-카르복실레이트을 사용하여 제조하였다. 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. 수율; 60 mg (71％); (M+H) 573.3.As shown in Scheme 7, it was prepared using (S) -tert-butyl 4- (4-aminophenyl) -3-methylpiperazin-1-carboxylate in the urea formation step. Upon urea formation, the Boc-piperazine intermediate was treated with TFA to afford the title compound. yield; 60 mg (71%); (M + H) 573.3.

(S)-tert-부틸 4-(4-아미노페닐)-3-메틸피페라진-1-카르복실레이트의 제조:Preparation of (S) -tert-butyl 4- (4-aminophenyl) -3-methylpiperazine-1-carboxylate:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 424: 1-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-((R)-3-메틸피페라진-1-일)페닐)우레아의 제조:Example 424 1- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (4-((R) -3-methylpiperazin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 (R)-tert-부틸 4-(4-아미노페닐)-3-메틸피페라진-1-카르복실레이트를 사용하여 제조하였다. 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. 수율; 68 mg (90％); (M+H) 573.3.As shown in Scheme 7, it was prepared using (R) -tert-butyl 4- (4-aminophenyl) -3-methylpiperazin-1-carboxylate in the urea formation step. Upon urea formation, the Boc-piperazine intermediate was treated with TFA to afford the title compound. yield; 68 mg (90%); (M + H) 573.3.

(R)-tert-부틸 4-(4-아미노페닐)-3-메틸피페라진-1-카르복실레이트의 제조:Preparation of (R) -tert-butyl 4- (4-aminophenyl) -3-methylpiperazin-1-carboxylate:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 425: 1-(4-((3R,5S)-3,5-디메틸피페라진-1-일)페닐)-3-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아의 제조:Example 425 1- (4-((3R, 5S) -3,5-dimethylpiperazin-1-yl) phenyl) -3- (4- (4-((R) -3-methylmorpholino Preparation of) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 (3,5-시스)-tert-부틸 4-(4-아미노페닐)-3,5-디메틸피페라진-1-카르복실레이트를 사용하여 제조하였다. 우레아 형성에 따라, Boc-피페라진 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. 수율; 67 mg (77％); (M+H) 587.3.As shown in Scheme 7, it was prepared using (3,5-cis) -tert-butyl 4- (4-aminophenyl) -3,5-dimethylpiperazine-1-carboxylate in the urea forming step. Upon urea formation, the Boc-piperazine intermediate was treated with TFA to afford the title compound. yield; 67 mg (77%); (M + H) 587.3.

(3,5-시스)-tert-부틸 4-(4-아미노페닐)-3,5-디메틸피페라진-1-카르복실레이트의 제조:Preparation of (3,5-cis) -tert-butyl 4- (4-aminophenyl) -3,5-dimethylpiperazine-1-carboxylate:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 426: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-술폭시모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 제조:Example 426: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-sulfoxymorpholino-1,3,5-triazine- Preparation of 2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea:

반응식 6에 나타낸 바와 같이 제조하였다. 아세토니트릴 (1.5 ml) 및 물 (0.5 ml) 중 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-티오모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아 (0.020 g, 0.033 mmol)의 용액을 제조하고, 옥손 (0.020 g, 0.033 mmol)을 첨가하였다. 용액을 실온에서 16 시간 동안 교반하였다. 현탁액을 에틸 아세테이트로 희석하고, 포화 중탄산나트륨으로 세척하였다. 유기상을 염수로 세척하고, 건조시키고, 농축시킨 다음, HPLC (20 분에 걸쳐 물 중 5-95％ 아세토니트릴, 0.05％ TFA 완충액, 워터스 아틀란티스 컬럼)로 정제하여 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-술폭시모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아의 술폭시드의 TFA 염 (0.0029 g, 14％)을 백색 고체로서 수득하였다. (M+H) 618.4.Prepared as shown in Scheme 6. 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-thiomorpholino-1 in acetonitrile (1.5 ml) and water (0.5 ml) Prepare a solution of, 3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea (0.020 g, 0.033 mmol) and give oxone (0.020 g, 0.033 mmol) was added. The solution was stirred at rt for 16 h. The suspension was diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was washed with brine, dried, concentrated and purified by HPLC (5-95% acetonitrile in water, 0.05% TFA buffer, Waters Atlantis column over 20 minutes) to 1- (4- (4- ( 3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-sulfoxymorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- ( The TFA salt (0.0029 g, 14%) of the sulfoxide of 4-methylpiperazin-1-yl) phenyl) urea was obtained as a white solid. (M + H) 618.4.

실시예 427: (R)-1-(4-(2-(디메틸아미노)에톡시)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아의 제조:Example 427: (R) -1- (4- (2- (dimethylamino) ethoxy) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H Preparation of -pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 4-(2-(디메틸아미노)에톡시)아닐린을 사용하여 제조하였다. 수율; 34 mg (51％); (M+H) 562.3.As shown in Scheme 7, it was prepared using 4- (2- (dimethylamino) ethoxy) aniline in the urea formation step. yield; 34 mg (51%); (M + H) 562.3.

실시예 428: (R)-1-(4-(4-에틸피페라진-1-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아의 제조:Example 428: (R) -1- (4- (4-ethylpiperazin-1-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro- Preparation of 2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-에틸피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 66 mg (93％); (M+H) 587.3.As shown in Scheme 7, it was prepared using commercially available 4- (4-ethylpiperazin-1-yl) aniline in the urea forming step. yield; 66 mg (93%); (M + H) 587.3.

실시예 429: (R)-1-(4-(4-이소프로필피페라진-1-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아의 제조:Example 429: (R) -1- (4- (4-isopropylpiperazin-1-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro Preparation of -2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 4-(4-이소프로필피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 66 mg (91％); (M+H) 601.4.As shown in Scheme 7, it was prepared using 4- (4-isopropylpiperazin-1-yl) aniline in the urea formation step. yield; 66 mg (91%); (M + H) 601.4.

4-(4-이소프로필피페라진-1-일)아닐린의 제조:Preparation of 4- (4-isopropylpiperazin-1-yl) aniline:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 430: (R)-1-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아의 제조:Example 430: (R) -1- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- Preparation of (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 1-(4-아미노페닐)-N,N-디메틸피페리딘-4-아민을 사용하여 제조하였다. 수율; 69 mg (95％); (M+H) 601.4.As shown in Scheme 7, it was prepared using 1- (4-aminophenyl) -N, N-dimethylpiperidin-4-amine in the urea formation step. yield; 69 mg (95%); (M + H) 601.4.

실시예 431: (R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아의 제조:Example 431: (R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(4-메틸피페라진-1-일)메타논을 사용하여 제조하였다. 수율; 38 mg (52％); (M+H) 601.3.As shown in Scheme 7, it was prepared using (4-aminophenyl) (4-methylpiperazin-1-yl) methanone in the urea formation step. yield; 38 mg (52%); (M + H) 601.3.

반응식 8에 나타낸 바와 같이 제조된 (4-아미노페닐)(피페라진-1-일)메타논 중간체를 사용하여 다음의 화합물을 제조하였다.The following compound was prepared using (4-aminophenyl) (piperazin-1-yl) methanone intermediate prepared as shown in Scheme 8.

실시예 432: (R)-1-(4-(4-이소프로필피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아의 제조:Example 432: (R) -1- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetra Preparation of Hydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(4-이소프로필피페라진-1-일)메타논을 사용하여 제조하였다. 수율; 68 mg (89％); (M+H) 629.3.As shown in Scheme 7, it was prepared using (4-aminophenyl) (4-isopropylpiperazin-1-yl) methanone in the urea formation step. yield; 68 mg (89%); (M + H) 629.3.

(4-아미노페닐)(4-이소프로필피페라진-1-일)메타논의 제조:Preparation of (4-aminophenyl) (4-isopropylpiperazin-1-yl) methanone:

4-니트로벤조일 클로라이드 및 적절한 아민으로부터 반응식 8에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 8 from 4-nitrobenzoyl chloride and appropriate amine.

실시예 433: (R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-일)피리딘-3-일)우레아의 제조:Example 433: (R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine-2 Preparation of -yl) phenyl) -3- (6- (4-methylpiperazin-1-yl) pyridin-3-yl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 6-(4-메틸피페라진-1-일)피리딘-3-아민을 사용하여 제조하였다. 수율; 69 mg (99％); (M+H) 574.3.As shown in Scheme 7, it was prepared using a commercially available 6- (4-methylpiperazin-1-yl) pyridin-3-amine in the urea forming step. yield; 69 mg (99%); (M + H) 574.3.

실시예 434: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아의 제조:Example 434: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-에틸피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 32 mg (43％); (M+H) 599.3.As shown in Scheme 7, it was prepared using commercially available 4- (4-ethylpiperazin-1-yl) aniline in the urea forming step. yield; 32 mg (43%); (M + H) 599.3.

실시예 435: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-일)페닐)우레아의 제조:Example 435: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 4-(4-이소프로필피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 51 mg (66％); (M+H) 613.4.As shown in Scheme 7, it was prepared using 4- (4-isopropylpiperazin-1-yl) aniline in the urea formation step. yield; 51 mg (66%); (M + H) 613.4.

실시예 436: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-시클로프로필피페라진-1-일)페닐)우레아의 제조:Example 436: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-cyclopropylpiperazin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 4-(4-시클로프로필피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 11 mg (14％); (M+H) 611.3.As shown in Scheme 7, it was prepared using 4- (4-cyclopropylpiperazin-1-yl) aniline in the urea formation step. yield; 11 mg (14%); (M + H) 611.3.

4-(4-시클로프로필피페라진-1-일)아닐린의 제조:Preparation of 4- (4-cyclopropylpiperazin-1-yl) aniline:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 437: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)우레아의 제조:Example 437: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 1-(4-아미노페닐)-N,N-디메틸피페리딘-4-아민을 사용하여 제조하였다. 수율; 28 mg (36％); (M+H) 613.4.As shown in Scheme 7, it was prepared using 1- (4-aminophenyl) -N, N-dimethylpiperidin-4-amine in the urea formation step. yield; 28 mg (36%); (M + H) 613.4.

실시예 438: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아의 제조:Example 438: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(4-메틸피페라진-1-일)메타논을 사용하여 제조하였다. 수율; 36 mg (46％); (M+H) 613.3.As shown in Scheme 7, it was prepared using (4-aminophenyl) (4-methylpiperazin-1-yl) methanone in the urea formation step. yield; 36 mg (46%); (M + H) 613.3.

실시예 439: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아의 제조:Example 439 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(4-이소프로필피페라진-1-일)메타논을 사용하여 제조하였다. 수율; 41 mg (50％); (M+H) 641.3.As shown in Scheme 7, it was prepared using (4-aminophenyl) (4-isopropylpiperazin-1-yl) methanone in the urea formation step. yield; 41 mg (50%); (M + H) 641.3.

하기의 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-우레아 화합물을 반응식 9에 나타낸 바와 같이 제조하였다.1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1,3, 5-triazin-2-yl) phenyl) -3-urea compound was prepared as shown in Scheme 9.

실시예 440: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아의 제조:Example 440: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-yl) phenyl) urea:

단계 1: (R)-4-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-메틸모르폴린의 제조:Step 1: Preparation of (R) -4- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-methylmorpholine:

아세톤 (20 mL) 및 빙수 (20 mL) 중 2,4-디클로로-6-(4-니트로페닐)-1,3,5-트리아진 (1.25 g, 4.61 mmol) 및 중탄산나트륨 (0.775 g, 9.22 mmol)의 용액을 제조하였다. 여기에 (R)-3-메틸모르폴린 (0.466 g, 4.61 mmol)을 5 분에 걸쳐 적가하였다. 생성된 황갈색 용액을 0℃에서 2 시간 동안 교반되도록 한 후에, 18 시간에 걸쳐 점차 실온으로 가온시켰다. 밝은 갈색 현탁액을 여과하고, 물로 세척하여 (R)-4-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-메틸모르폴린 (1.40 g, 90％)을 밝은 갈색 고체로서 수득하였다. HRMS 336.0857 (M+H, 계산치), 336.0845 (M+H, 관측치).2,4-dichloro-6- (4-nitrophenyl) -1,3,5-triazine (1.25 g, 4.61 mmol) and sodium bicarbonate (0.775 g, 9.22 in acetone (20 mL) and ice water (20 mL) mmol) was prepared. To this was added (R) -3-methylmorpholine (0.466 g, 4.61 mmol) dropwise over 5 minutes. The resulting tan solution was allowed to stir at 0 ° C. for 2 hours and then gradually warmed to room temperature over 18 hours. The light brown suspension is filtered and washed with water to give (R) -4- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-methylmorpholine ( 1.40 g, 90%) was obtained as a light brown solid. HRMS 336.0857 (M + H, calculated), 336.0845 (M + H, found).

단계 2: 8-(4-((R)-3-메틸모르폴리노)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄의 제조:Step 2: 8- (4-((R) -3-methylmorpholino) -6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8- Preparation of Azabicyclo [3.2.1] octane:

아세톤 (10 mL) 및 빙수 (10 mL) 중 (R)-4-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-메틸모르폴린 (0.94 g, 2.80 mmol)의 용액을 제조하였다. 여기에 아세톤 (10 mL) 및 물 (10 mL) 중 3-옥사-8-아자비시클로[3.2.1]옥탄-히드로클로라이드 (0.419 g, 2.80 mmol) 및 중탄산나트륨 (0.470 g, 5.60 mmol)의 현탁액을 10 분에 걸쳐 적가하였다. 생성된 황갈색 용액을 0℃에서 2 시간 동안 교반되도록 한 후에, 3 시간에 걸쳐 점차 실온으로 가온시켰다. 밝은 갈색 현탁액을 여과하고 물로 세척하여 8-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.964 g, 83％)을 갈색 고체로서 수득하였다. HRMS 413.1931 (M+H, 계산치), 413.1936 (M+H, 관측치).(R) -4- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-methylmorph in acetone (10 mL) and ice water (10 mL) A solution of Pauline (0.94 g, 2.80 mmol) was prepared. Here suspension of 3-oxa-8-azabicyclo [3.2.1] octane-hydrochloride (0.419 g, 2.80 mmol) and sodium bicarbonate (0.470 g, 5.60 mmol) in acetone (10 mL) and water (10 mL) Was added dropwise over 10 minutes. The resulting tan solution was allowed to stir at 0 ° C. for 2 hours and then gradually warmed to room temperature over 3 hours. The light brown suspension was filtered and washed with water to afford 8- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2. 1] octane (0.964 g, 83%) was obtained as a brown solid. HRMS 413.1931 (M + H, calculated), 413.1936 (M + H, observed).

단계 3: 4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)아닐린의 제조:Step 3: 4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1,3,5- Preparation of Triazin-2-yl) aniline:

에틸 아세테이트 (10 ml), 메탄올 (10 ml) 및 메틸렌 클로라이드 (5 ml - EA/메탄올 중 SM의 불량한 용해도 때문에 첨가함) 중 8-(4-((R)-3-메틸모르폴리노)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-3-옥사-8-아자비시클로[3.2.1]옥탄 (0.915 g, 2.22 mmol)의 용액을 제조하고, 10％ 탄소상 팔라듐 (0.270 g, 30 중량％)을 첨가하였다. 플라스크를 수소 기체 (풍선)로 퍼징시키고, 수소 양압 하에 16 시간 동안 교반되도록 하였다. 현탁액을 셀라이트™를 통해 여과하고, 필터 케이크를 에틸 아세테이트로 세척하고, 여과물을 농축시켜 4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)아닐린 (0.587 g, 69％)을 회백색 고체로서 수득하였다. (M+H) 383.3.8- (4-((R) -3-methylmorpholino)-in ethyl acetate (10 ml), methanol (10 ml) and methylene chloride (5 ml-added because of poor solubility of SM in EA / methanol) Prepare a solution of 6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -3-oxa-8-azabicyclo [3.2.1] octane (0.915 g, 2.22 mmol), Palladium on carbon 10% (0.270 g, 30% by weight) was added. The flask was purged with hydrogen gas (balloon) and allowed to stir for 16 hours under positive hydrogen pressure. The suspension is filtered through Celite ™, the filter cake is washed with ethyl acetate and the filtrate is concentrated to 4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl)- 6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) aniline (0.587 g, 69%) was obtained as off-white solid. (M + H) 383.3.

단계 4: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아의 제조:Step 4: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1,3 Preparation of, 5-triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-yl) phenyl) urea:

반응식 1에 기재된, 메틸렌 클로라이드 중 트리포스겐 및 트리에틸아민을 사용하는 우레아 형성 방법은 시판 구입가능한 4-(4-에틸피페라진-1-일)아닐린을 아민 성분으로서 사용하여 활용하였다. HPLC (20 분에 걸쳐 물 중 5-95％ 아세토니트릴, 0.05％ TFA 완충액, 워터스 아틀란티스 컬럼)로 정제하여 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아 (0.0761 g, 95％)을 밝은 황색 고체로서 수득하였다. (M+H) 614.3.The urea formation method using triphosgene and triethylamine in methylene chloride, described in Scheme 1, was utilized using commercially available 4- (4-ethylpiperazin-1-yl) aniline as the amine component. Purification by HPLC (5-95% acetonitrile in water, 0.05% TFA buffer, Waters Atlantis column over 20 minutes) to 1- (4- (4- (3- (oxa-8-azabicyclo [3.2.1] octane) -8-yl) -6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1 -Yl) phenyl) urea (0.0761 g, 95%) was obtained as a light yellow solid. (M + H) 614.3.

실시예 441: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-일)페닐)우레아의 제조:Example 441: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-yl) phenyl) urea:

반응식 9에 나타낸 바와 같이, 우레아 형성 단계에서 4-(4-이소프로필피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 82 mg (100％); (M+H) 628.4.As shown in Scheme 9, it was prepared using 4- (4-isopropylpiperazin-1-yl) aniline in the urea formation step. yield; 82 mg (100%); (M + H) 628.4.

실시예 442: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-시클로프로필피페라진-1-일)페닐)우레아의 제조:Example 442: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-cyclopropylpiperazin-1-yl) phenyl) urea:

반응식 9에 나타낸 바와 같이, 우레아 형성 단계에서 4-(4-시클로프로필피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 32 mg (39％); (M+H) 626.3.As shown in Scheme 9, it was prepared using 4- (4-cyclopropylpiperazin-1-yl) aniline in the urea formation step. yield; 32 mg (39%); (M + H) 626.3.

실시예 443: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)우레아의 제조:Example 443: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) urea:

반응식 9에 나타낸 바와 같이, 우레아 형성 단계에서 1-(4-아미노페닐)-N,N-디메틸피페리딘-4-아민을 사용하여 제조하였다. 수율; 77 mg (93％); (M+H) 628.4.As shown in Scheme 9, 1- (4-aminophenyl) -N, N-dimethylpiperidin-4-amine was prepared in the urea formation step. yield; 77 mg (93%); (M + H) 628.4.

실시예 444: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아의 제조:Example 444: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea:

반응식 9에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(4-메틸피페라진-1-일)메타논을 사용하여 제조하였다. 수율; 43 mg (52％); (M+H) 628.3.As shown in Scheme 9, it was prepared using (4-aminophenyl) (4-methylpiperazin-1-yl) methanone in the urea formation step. yield; 43 mg (52%); (M + H) 628.3.

실시예 445: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아의 제조:Example 445: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea:

반응식 9에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(4-이소프로필피페라진-1-일)메타논을 사용하여 제조하였다. 수율; 72 mg (84％); (M+H) 656.4.As shown in Scheme 9, (4-aminophenyl) (4-isopropylpiperazin-1-yl) methanone was prepared in the urea formation step. yield; 72 mg (84%); (M + H) 656.4.

실시예 446: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-일)피리딘-3-일)우레아의 제조:Example 446 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6-((R) -3-methylmorpholino) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (6- (4-methylpiperazin-1-yl) pyridin-3-yl) urea:

반응식 9에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 6-(4-메틸피페라진-1-일)피리딘-3-아민을 사용하여 제조하였다. 수율; 74 mg (94％); (M+H) 601.3.As shown in Scheme 9, it was prepared using a commercially available 6- (4-methylpiperazin-1-yl) pyridin-3-amine in the urea forming step. yield; 74 mg (94%); (M + H) 601.3.

실시예 447: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아의 제조:Example 447: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of 4-ethylpiperazin-1-yl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(4-에틸피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 80 mg (99％); (M+H) 602.3.As shown in Scheme 1, a commercially available 4- (4-ethylpiperazin-1-yl) aniline was prepared in the urea forming step. yield; 80 mg (99%); (M + H) 602.3.

실시예 448: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-일)페닐)우레아의 제조:Example 448: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of 4-isopropylpiperazin-1-yl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 4-(4-이소프로필피페라진-1-일)아닐린을 사용하여 제조하였다. 수율; 74 mg (88％); (M+H) 616.4.As shown in Scheme 1, it was prepared using 4- (4-isopropylpiperazin-1-yl) aniline in the urea formation step. yield; 74 mg (88%); (M + H) 616.4.

실시예 449: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)우레아의 제조:Example 449 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of 4- (dimethylamino) piperidin-1-yl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 1-(4-아미노페닐)-N,N-디메틸피페리딘-4-아민을 사용하여 제조하였다. 수율; 80 mg (96％); (M+H) 616.4.As shown in Scheme 1, 1- (4-aminophenyl) -N, N-dimethylpiperidin-4-amine was prepared in the urea formation step. yield; 80 mg (96%); (M + H) 616.4.

실시예 450: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아의 제조:Example 450: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of 4-methylpiperazin-1-carbonyl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(4-메틸피페라진-1-일)메타논을 사용하여 제조하였다. 수율; 79 mg (95％); (M+H) 616.3.As shown in Scheme 1, (4-aminophenyl) (4-methylpiperazin-1-yl) methanone was prepared in the urea formation step. yield; 79 mg (95%); (M + H) 616.3.

실시예 451: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아의 제조:Example 451 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of 4-isopropylpiperazin-1-carbonyl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(4-이소프로필피페라진-1-일)메타논을 사용하여 제조하였다. 수율; 18 mg (20％); (M+H) 644.4.As shown in Scheme 1, (4-aminophenyl) (4-isopropylpiperazin-1-yl) methanone was prepared in the urea formation step. yield; 18 mg (20%); (M + H) 644.4.

실시예 452: 4-(3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레이도)-N,N-디메틸벤즈아미드의 제조:Example 452: 4- (3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) ureido)- Preparation of N, N-dimethylbenzamide:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-아미노-N,N-디메틸벤즈아미드를 사용하여 제조하였다. 수율; 43 mg (57％); (M+H) 561.3.As shown in Scheme 1, a commercially available 4-amino-N, N-dimethylbenzamide was prepared in the urea forming step. yield; 43 mg (57%); (M + H) 561.3.

실시예 453: 1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피롤리딘-1-일메틸)페닐)우레아의 제조:Example 453: 1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- ( Preparation of Pyrrolidin-1-ylmethyl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-(피롤리딘-1-일메틸)아닐린을 사용하여 제조하였다. 수율; 61 mg (79％); (M+H) 573.3.As shown in Scheme 1, it was prepared using commercially available 4- (pyrrolidin-1-ylmethyl) aniline in the urea forming step. yield; 61 mg (79%); (M + H) 573.3.

실시예 454: 4-(3-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드의 제조:Example 454: 4- (3- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) Preparation of -1,3,5-triazin-2-yl) phenyl) ureido) benzamide:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-아미노벤즈아미드를 사용하여 제조하였다. 수율; 22 mg (21％); (M+H) 530.2.As shown in Scheme 7, it was prepared using commercially available 4-aminobenzamide in the urea forming step. yield; 22 mg (21%); (M + H) 530.2.

실시예 455: 4-(3-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)-N,N-디메틸벤즈아미드의 제조:Example 455: 4- (3- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) Preparation of -1,3,5-triazin-2-yl) phenyl) ureido) -N, N-dimethylbenzamide:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 시판 구입가능한 4-아미노-N,N-디메틸벤즈아미드를 사용하여 제조하였다. 수율; 22 mg (21％); (M+H) 558.3.As shown in Scheme 7, it was prepared using commercially available 4-amino-N, N-dimethylbenzamide in the urea forming step. yield; 22 mg (21%); (M + H) 558.3.

실시예 456: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(피롤리딘-1-카르보닐)페닐)우레아의 제조:Example 456: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (pyrrolidine-1-carbonyl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(피롤리딘-1-일)메타논을 사용하여 제조하였다. 수율; 41 mg (36％); (M+H) 584.3.As shown in Scheme 7, it was prepared using (4-aminophenyl) (pyrrolidin-1-yl) methanone in the urea formation step. yield; 41 mg (36%); (M + H) 584.3.

(4-아미노페닐)(피롤리딘-1-일)메타논의 제조:Preparation of (4-aminophenyl) (pyrrolidin-1-yl) methanone:

4-니트로벤조일 클로라이드 및 적절한 아민으로부터 반응식 8에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 8 from 4-nitrobenzoyl chloride and appropriate amine.

실시예 457: 4-(3-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)벤즈아미드의 제조:Example 457: 4- (3- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) Preparation of -1,3,5-triazin-2-yl) phenyl) ureido) -N- (2- (dimethylamino) ethyl) benzamide:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 4-아미노-N-(2-(디메틸아미노)에틸)벤즈아미드를 사용하여 제조하였다. 수율; 36 mg (32％); (M+H) 601.3.As shown in Scheme 7, it was prepared using 4-amino-N- (2- (dimethylamino) ethyl) benzamide in the urea formation step. yield; 36 mg (32%); (M + H) 601.3.

4-아미노-N-(2-(디메틸아미노)에틸)벤즈아미드의 제조:Preparation of 4-amino-N- (2- (dimethylamino) ethyl) benzamide:

4-니트로벤조일 클로라이드 및 적절한 아민으로부터 반응식 8에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 8 from 4-nitrobenzoyl chloride and appropriate amine.

실시예 458: 4-(3-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(메틸아미노)에틸)벤즈아미드의 제조:Example 458: 4- (3- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) Preparation of -1,3,5-triazin-2-yl) phenyl) ureido) -N- (2- (methylamino) ethyl) benzamide:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 tert-부틸 2-(4-아미노벤즈아미도)에틸(메틸)카르바메이트를 사용하여 제조하였다. 우레아 형성에 따라, Boc-아민 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. 수율; 25 mg (22％); (M+H) 587.3.As shown in Scheme 7, it was prepared using tert-butyl 2- (4-aminobenzamido) ethyl (methyl) carbamate in the urea formation step. Upon urea formation, the Boc-amine intermediate was treated with TFA to afford the title compound. yield; 25 mg (22%); (M + H) 587.3.

tert-부틸 2-(4-아미노벤즈아미도)에틸(메틸)카르바메이트의 제조:Preparation of tert-butyl 2- (4-aminobenzamido) ethyl (methyl) carbamate:

4-니트로벤조일 클로라이드 및 적절한 아민으로부터 반응식 8에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 8 from 4-nitrobenzoyl chloride and appropriate amine.

실시예 459: 4-(3-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)-N-메틸벤즈아미드의 제조:Example 459: 4- (3- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) Preparation of -1,3,5-triazin-2-yl) phenyl) ureido) -N- (2- (dimethylamino) ethyl) -N-methylbenzamide

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 4-아미노-N-(2-(디메틸아미노)에틸)-N-메틸벤즈아미드를 사용하여 제조하였다. 수율; 10 mg (9％); (M+H) 615.3.As shown in Scheme 7, it was prepared using 4-amino-N- (2- (dimethylamino) ethyl) -N-methylbenzamide in the urea formation step. yield; 10 mg (9%); (M + H) 615.3.

4-아미노-N-(2-(디메틸아미노)에틸)-N-메틸벤즈아미드의 제조:Preparation of 4-amino-N- (2- (dimethylamino) ethyl) -N-methylbenzamide:

4-니트로벤조일 클로라이드 및 적절한 아민으로부터 반응식 8에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 8 from 4-nitrobenzoyl chloride and appropriate amine.

실시예 460: 1-(4-(4-(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(모르폴린-4-카르보닐)페닐)우레아의 제조:Example 460: 1- (4- (4- (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) -6- (tetrahydro-2H-pyran-4-yl) -1, Preparation of 3,5-triazin-2-yl) phenyl) -3- (4- (morpholin-4-carbonyl) phenyl) urea:

반응식 7에 나타낸 바와 같이, 우레아 형성 단계에서 (4-아미노페닐)(모르폴리노)메타논을 사용하여 제조하였다. 수율; 25 mg (21％); (M+H) 600.3.As shown in Scheme 7, it was prepared using (4-aminophenyl) (morpholino) methanone in the urea formation step. yield; 25 mg (21%); (M + H) 600.3.

(4-아미노페닐)(모르폴리노)메타논의 제조:Preparation of (4-aminophenyl) (morpholino) methanone:

4-니트로벤조일 클로라이드 및 적절한 아민으로부터 반응식 8에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 8 from 4-nitrobenzoyl chloride and appropriate amine.

실시예 461: 1-(4-(2-아미노에틸아미노)페닐)-3-(4-(4,6-디(3-옥사-8-아자비시클로[3.2.1]옥탄-8-일)-1,3,5-트리아진-2-일)페닐)우레아의 제조:Example 461: 1- (4- (2-aminoethylamino) phenyl) -3- (4- (4,6-di (3-oxa-8-azabicyclo [3.2.1] octan-8-yl) Preparation of -1,3,5-triazin-2-yl) phenyl) urea:

반응식 1에 나타낸 바와 같이, 우레아 형성 단계에서 디-Boc 보호된 N1-(2-아미노에틸)벤젠-1,4-디아민을 사용하여 제조하였다. 우레아 형성에 따라, 디-Boc-아민 중간체를 TFA로 처리하여 표제 화합물을 수득하였다. As shown in Scheme 1, di-Boc protected N1- (2-aminoethyl) benzene-1,4-diamine was prepared in the urea formation step. Upon urea formation, the di-Boc-amine intermediate was treated with TFA to afford the title compound.

Figure 112010076169004-pct00070
Figure 112010076169004-pct00070

디-Boc 보호된 N1-(2-아미노에틸)벤젠-1,4-디아민의 제조:Preparation of di-Boc protected N1- (2-aminoethyl) benzene-1,4-diamine:

4-플루오로니트로벤젠 및 적절한 아민으로부터 반응식 4에 나타낸 바와 같이 제조하였다.Prepared as shown in Scheme 4 from 4-fluoronitrobenzene and appropriate amines.

실시예 462: 4-({[4-(4-{4-[(메틸카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드의 제조Example 462: 4-({[4- (4- {4-[(methylcarbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl ) Phenyl] carbamoyl} amino) benzamide

단계 1: 페닐 4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)페닐카르바메이트의 제조Step 1: Preparation of Phenyl 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenylcarbamate

무수 디클로로메탄 (250 mL) 중 4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)아닐린 (25.0 g, 114 mmol) 및 피리딘 (4 mL, 57 mmol)의 용액에 페닐 클로로포르메이트 (12 mL, 114 mmol)를 -10℃에서 적가하였다. 반응 혼합물을 -10℃에서 30 분 동안 교반한 후에, 실온에서 30 분 동안 교반하였다. 반응 혼합물을 디클로로메탄 (100 mL)으로 희석하고, 물 (2 x 70 mL)로 세척하였다. 유기층을 무수 Na2SO4 상에서 건조시키고, 농축시켜 조 생성물을 수득하였다. 이어서, 조 생성물을 디에틸 에테르 (15 mL) 중에 용해시키고, 10 분 동안 음파처리한 후에, 펜탄 (30 mL)을 첨가하였다. 생성된 고체를 여과하고, 펜탄으로 세척하여 페닐 4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)페닐카르바메이트를 수득하였다 (26 g, 88％ 수율).4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (25.0 g, 114 mmol) and pyridine (4 mL in anhydrous dichloromethane (250 mL) , 57 mmol) was added dropwise phenyl chloroformate (12 mL, 114 mmol) at -10 ° C. The reaction mixture was stirred at −10 ° C. for 30 minutes and then at room temperature for 30 minutes. The reaction mixture was diluted with dichloromethane (100 mL) and washed with water (2 x 70 mL). The organic layer was dried over anhydrous Na 2 SO 4 and concentrated to give crude product. The crude product was then dissolved in diethyl ether (15 mL) and sonicated for 10 minutes before pentane (30 mL) was added. The resulting solid was filtered and washed with pentane to afford phenyl 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenylcarbamate (26 g, 88% yield).

Figure 112010076169004-pct00071
Figure 112010076169004-pct00071

단계 2: 1-메틸-3-(4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)페닐) 우레아의 제조Step 2: Preparation of 1-methyl-3- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) urea

THF 150 mL 중 페닐 4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)페닐카르바메이트 (26 g, 76.6 mmol), 2.0M 메틸아민/THF (265 mL, 530 mmol)의 혼합물을 실온에서 6 시간 동안 교반한 후에, 과량의 용매를 반응 혼합물로부터 증류 제거하고; 잔류물을 물 중에 용해시키고, 에틸 아세테이트로 추출하였다. 유기층을 무수 Na2SO4 상에서 건조시키고, 감압하에 농축시켰다. 조 생성물을 석유 에테르 중 5-60％ 에틸 아세테이트를 용리액으로서 사용하여 실리카겔 컬럼 크로마토그래피로 정제하여 1-메틸-3-[4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보롤란-2-일)-페닐]-우레아 (20 g, 88％ 수율)를 백색 고체로서 수득하였다.Phenyl 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenylcarbamate (26 g, 76.6 mmol) in 150 mL THF, 2.0 M methylamine / THF (265 mL, 530 mmol) was stirred at RT for 6 h, then excess solvent was distilled off from the reaction mixture; The residue was dissolved in water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na 2 S0 4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 5-60% ethyl acetate in petroleum ether as eluent to give 1-methyl-3- [4- (4,4,5,5-tetramethyl- [1,3, 2] dioxaborolan-2-yl) -phenyl] -urea (20 g, 88% yield) was obtained as a white solid.

Figure 112010076169004-pct00072
Figure 112010076169004-pct00072

단계 3: 4-(4,6-디클로로-1,3,5-트리아진-2-일)모르폴린의 제조Step 3: Preparation of 4- (4,6-dichloro-1,3,5-triazin-2-yl) morpholine

모르폴린 (9.5 mL, 108 mmol)을 클로로포름 (10 mL) 중 시아누르산 클로라이드 (20 g, 108 mmol)의 용액에 첨가하고, -5℃에서 1 시간 동안 교반하였다. 반응 혼합물을 물로 희석하고, 디클로로메탄으로 추출하였다. 유기층을 무수 Na2SO4 상에서 건조시키고, 여과하고, 감압하에 농축시켰다. 조 생성물을 석유 에테르 중 5％ 에틸 아세테이트를 용리액으로서 사용하는 실리카겔 (100-200 메쉬) 컬럼 크로마토그래피로 정제하여 4-(4,6-디클로로-1,3,5-트리아진-2-일)모르폴린 (10 g, 39％ 수율)을 수득하였다.Morpholine (9.5 mL, 108 mmol) was added to a solution of cyanuric chloride (20 g, 108 mmol) in chloroform (10 mL) and stirred at -5 ° C for 1 hour. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was dried over anhydrous Na 2 SO 4 , filtered and concentrated under reduced pressure. The crude product was purified by silica gel (100-200 mesh) column chromatography using 5% ethyl acetate in petroleum ether as eluent to afford 4- (4,6-dichloro-1,3,5-triazin-2-yl). Morpholine (10 g, 39% yield) was obtained.

단계 4: 1-(4-(4-클로로-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-메틸우레아의 제조Step 4: Preparation of 1- (4- (4-chloro-6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-methylurea

탈기된 1,2-디메톡시에탄 (400 mL) 중 화합물 4-(4,6-디클로로-1,3,5-트리아진-2-일)모르폴린 (10 g, 42.7 mmol), Pd(PPh3)4 (2.46 g, 2.1 mmol), 1-메틸-3-[4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보롤란-2-일)-페닐]-우레아 (11.7 g, 42.4 mmol) 및 1N Na2CO3 (168 mL, 168 mmol)의 혼합물을 8 시간 동안 N2 분위기 하에 65℃로 가열하였다. 반응 혼합물을 여과하고, 물로 희석하고, 에틸 아세테이트로 추출하고, 물, 염수로 세척하고, 무수 Na2SO4 상에서 건조시키고, 여과하고 감압하에 농축시켰다. 조 생성물을 석유 에테르 중 20-60％ 에틸 아세테이트를 용리액으로서 사용하는 실리카겔 (100-200 메쉬) 컬럼 크로마토그래피로 정제하여 1-(4-(4-클로로-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 (5.0 g, 34％ 수율)를 수득하였다.Compound 4- (4,6-dichloro-1,3,5-triazin-2-yl) morpholine (10 g, 42.7 mmol), Pd (PPh in degassed 1,2-dimethoxyethane (400 mL) 3 ) 4 (2.46 g, 2.1 mmol), 1-methyl-3- [4- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -phenyl ] -Urea (11.7 g, 42.4 mmol) and 1N Na 2 CO 3 (168 mL, 168 mmol) were heated to 65 ° C. under N 2 atmosphere for 8 h. The reaction mixture was filtered, diluted with water, extracted with ethyl acetate, washed with water, brine, dried over anhydrous Na 2 SO 4 , filtered and concentrated under reduced pressure. The crude product was purified by silica gel (100-200 mesh) column chromatography using 20-60% ethyl acetate in petroleum ether as eluent to give 1- (4- (4-chloro-6-morpholino-1,3, 5-triazin-2-yl) phenyl) -3-methylurea (5.0 g, 34% yield) was obtained.

Figure 112010076169004-pct00073
Figure 112010076169004-pct00073

단계 5: 1-(4-(4-(4-아미노페닐)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-메틸우레아의 제조Step 5: Preparation of 1- (4- (4- (4-aminophenyl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-methylurea

표제 화합물을 실시예 462 단계 4의 절차에 따라 1-(4-(4-클로로-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)아닐린을 사용하여 제조하였다. 수득량 2 g, 45％ 수율.The title compound was prepared according to the procedure of Example 462 step 4 in 1- (4- (4-chloro-6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-methylurea and 4 Prepared using-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline. Yield 2 g, 45% yield.

단계 6: 페닐 4-카르바모일페닐카르바메이트의 제조Step 6: Preparation of Phenyl 4-carbamoylphenylcarbamate

무수 CH2Cl2 (100 mL) 중 4-아미노벤즈아미드 (5.0 g, 36.7 mmol) 및 피리딘 (2.9 g, 36.7 mmol)의 용액에 -10℃에서 페닐 클로로포르메이트 (6.9 g, 44.1 mmol)를 적가하고, -10℃에서 30 분 동안 교반한 후에, 실온에서 30 분 동안 교반하였다. 반응 혼합물을 CH2Cl2 (100 mL)로 희석하고, 물 (2 x 70 mL)로 세척하였다. 유기층을 무수 Na2SO4 상에서 건조시키고, 농축시켜 조 생성물을 얻었다. 조 생성물을 디에틸 에테르 (15 mL) 중에 용해시키고, 10 분 동안 음파처리한 후에, 펜탄 (30 mL)을 첨가하고, 생성된 고체를 여과하고, 펜탄으로 세척하여 페닐 4-카르바모일페닐카르바메이트 (7.2 g, 77％ 수율)를 수득하였다.To a solution of 4-aminobenzamide (5.0 g, 36.7 mmol) and pyridine (2.9 g, 36.7 mmol) in anhydrous CH 2 Cl 2 (100 mL) was charged phenyl chloroformate (6.9 g, 44.1 mmol) at −10 ° C. It was added dropwise and stirred at −10 ° C. for 30 minutes and then at room temperature for 30 minutes. The reaction mixture was diluted with CH 2 Cl 2 (100 mL) and washed with water (2 × 70 mL). The organic layer was dried over anhydrous Na 2 SO 4 and concentrated to give the crude product. The crude product was dissolved in diethyl ether (15 mL), sonicated for 10 minutes, then pentane (30 mL) was added and the resulting solid was filtered and washed with pentane to phenyl 4-carbamoylphenylcart Barmate (7.2 g, 77% yield) was obtained.

단계 7: 4-({[4-(4-{4-[(메틸카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드의 제조Step 7: 4-({[4- (4- {4-[(methylcarbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) Preparation of Phenyl] carbamoyl} amino) benzamide

무수 DMF (10 mL) 중 1-(4-(4-(4-아미노페닐)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 (0.6 g, 1.5 mmol) 및 트리에틸아민 (4-5 mL)의 용액에, 페닐 4-카르바모일페닐카르바메이트 (1.15 g, 4.5 mmol)를 실온에서 첨가하고, 혼합물을 10 시간 동안 질소 분위기 하에 90℃로 가열하였다. 실온으로 냉각시킨 후, 반응 혼합물을 빙수로 켄칭하고, 생성된 고체를 여과하여 조 생성물을 얻었다. 조 생성물을 정제용 HPLC로 정제하여 4-({[4-(4-{4-[(메틸카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드 (45 mg, 5.3％ 수율)를 수득하였다.1- (4- (4- (4-aminophenyl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-methylurea (0.6 in anhydrous DMF (10 mL) g, 1.5 mmol) and triethylamine (4-5 mL), phenyl 4-carbamoylphenylcarbamate (1.15 g, 4.5 mmol) is added at room temperature and the mixture is kept under nitrogen atmosphere for 10 hours. Heated to 90 ° C. After cooling to room temperature, the reaction mixture was quenched with ice water and the resulting solid was filtered to afford the crude product. The crude product was purified by preparative HPLC to give 4-({[4- (4- {4-[(methylcarbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-tri Azin-2-yl) phenyl] carbamoyl} amino) benzamide (45 mg, 5.3% yield) was obtained.

실시예 463: 1-{4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조Example 463: 1- {4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-tri Preparation of Azin-2-yl] phenyl} -3-pyridin-3-ylurea

단계 1: 4-(4,6-디클로로-1,3,5-트리아진-2-일)-3,5-디메틸모르폴린의 제조Step 1: Preparation of 4- (4,6-dichloro-1,3,5-triazin-2-yl) -3,5-dimethylmorpholine

표제 화합물을 실시예 462 단계 3의 절차에 따라 시아누르산 클로라이드 및 3,5-디메틸모르폴린을 사용하여 제조하였다. 수득량 5 g, 35％ 수율.The title compound was prepared using cyanuric chloride and 3,5-dimethylmorpholine following the procedure of Example 462 step 3. Yield 5 g, 35% yield.

Figure 112010076169004-pct00074
Figure 112010076169004-pct00074

단계 2: 1-(4-(4-클로로-6-(3,5-디메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아의 제조Step 2: Preparation of 1- (4- (4-chloro-6- (3,5-dimethylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3-methylurea

표제 화합물을 실시예 462 단계 4의 절차에 따라 4-(4,6-디클로로-1,3,5-트리아진-2-일)-3,5-디메틸모르폴린 및 1-메틸-3-[4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보롤란-2-일)-페닐]-우레아를 사용하여 제조하였다. 수득량 1.15 g, 16％ 수율.The title compound was purified by the procedure of Example 462 step 4 according to the procedure of 4- (4,6-dichloro-1,3,5-triazin-2-yl) -3,5-dimethylmorpholine and 1-methyl-3- [ Prepared using 4- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -phenyl] -urea. Yield 1.15 g, 16% yield.

단계 3: 1-(4-(4-(4-아미노페닐)-6-(3,5-디메틸 모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아의 제조Step 3: 1- (4- (4- (4-aminophenyl) -6- (3,5-dimethyl morpholino) -1,3,5-triazin-2-yl) phenyl) -3-methyl Manufacture of urea

표제 화합물을 실시예 462 단계 4의 절차에 따라 1-(4-(4-클로로-6-(3,5-디메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)아닐린을 사용하여 제조하였다. 수득량 2 g, 86％ 수율.The title compound was prepared according to the procedure of Example 462 step 4 in 1- (4- (4-chloro-6- (3,5-dimethylmorpholino) -1,3,5-triazin-2-yl) phenyl) Prepared using -3-methylurea and 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline. Yield 2 g, 86% yield.

단계 4: 페닐 피리딘-3-일카르바메이트의 제조Step 4: Preparation of Phenyl Pyridin-3-ylcarbamate

표제 화합물을 실시예 462 단계 6의 절차에 따라 3-아미노피리딘 및 페닐 클로로포르메이트를 사용하여 제조하였다. 수득량 7 g, 62％ 수율.The title compound was prepared using 3-aminopyridine and phenyl chloroformate following the procedure of Example 462 step 6. Yield 7 g, 62% yield.

단계 5: 1-{4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아의 제조Step 5: 1- {4- [4- (3,5-Dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-triazine -2-yl] phenyl} -3-pyridin-3-ylurea

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-(3,5-디메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 피리딘-3-일카르바메이트를 사용하여 제조하였다. 수득량 77 mg, 6％ 수율.The title compound was purified according to the procedure of Example 462 step 7, 1- (4- (4- (4-aminophenyl) -6- (3,5-dimethylmorpholino) -1,3,5-triazine-2 -Yl) phenyl) -3-methylurea and phenyl pyridin-3-ylcarbamate. Yield 77 mg, 6% yield.

실시예 464: 4-[({4-[4-{4-[(메틸카르바모일)아미노]페닐}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조Example 464: 4-[({4- [4- {4-[(methylcarbamoyl) amino] phenyl} -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide

단계 1: 3-(4,6-디클로로-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄의 제조Step 1: Preparation of 3- (4,6-dichloro-1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane

표제 화합물을 실시예 462 단계 3의 절차에 따라 시아누르산 클로라이드 및 8-옥사-3-아자비시클로[3.2.1]옥탄을 사용하여 제조하였다. 수득량 10 g, 47％ 수율.The title compound was prepared using cyanuric chloride and 8-oxa-3-azabicyclo [3.2.1] octane following the procedure of Example 462 step 3. Yield 10 g, 47% yield.

단계 2: 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-1,3,5-트리아진-2-일)페닐)-3-메틸우레아의 제조Step 2: 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro-1,3,5-triazin-2-yl) phenyl Preparation of 3-methylurea

표제 화합물을 실시예 462 단계 4의 절차에 따라 3-(4,6-디클로로-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄 및 1-메틸-3-[4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보롤란-2-일)-페닐]-우레아를 사용하여 제조하였다. 수득량 5 g, 29％ 수율.The title compound was purified according to the procedure of Example 462 step 4 using 3- (4,6-dichloro-1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane and Prepared using 1-methyl-3- [4- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -phenyl] -urea. Yield 5 g, 29% yield.

단계 3: 1-(4-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아의 제조Step 3: 1- (4- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -1,3,5-triazine- Preparation of 2-yl) phenyl) -3-methylurea

표제 화합물을 실시예 462 단계 4의 절차에 따라 1-(4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-클로로-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)아닐린을 사용하여 제조하였다. 수득량 2.8 g, 49％ 수율.The title compound was prepared according to the procedure of Example 462 step 4 in 1- (4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-chloro-1,3,5 -Triazin-2-yl) phenyl) -3-methylurea and 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline It was. Yield 2.8 g, 49% yield.

단계 4: 4-[({4-[4-{4-[(메틸카르바모일)아미노]페닐}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조Step 4: 4-[({4- [4- {4-[(methylcarbamoyl) amino] phenyl} -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) Preparation of -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 4-카르바모일페닐카르바메이트를 사용하여 제조하였다. 수득량 90 mg, 13％ 수율.The title compound was prepared according to the procedure of Example 462 step 7 in 1- (4- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl)- 1,3,5-triazin-2-yl) phenyl) -3-methylurea and phenyl 4-carbamoylphenylcarbamate. Yield 90 mg, 13% yield.

실시예 465: 3-[({4-[4-{4-[(메틸카르바모일)아미노]페닐}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조Example 465: 3-[({4- [4- {4-[(methylcarbamoyl) amino] phenyl} -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl ) -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide

단계 1: 페닐 3-카르바카르바모일페닐카르바메이트의 제조Step 1: Preparation of Phenyl 3-carbacarbamoylphenylcarbamate

표제 화합물을 실시예 462 단계 6의 절차에 따라 3-아미노벤즈아미드 및 페닐 클로로포르메이트를 사용하여 제조하였다. 수득량 7 g, 74％ 수율.The title compound was prepared using 3-aminobenzamide and phenyl chloroformate following the procedure of Example 462 step 6. Yield 7 g, 74% yield.

단계 2: 3-[({4-[4-{4-[(메틸카르바모일)아미노]페닐}-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조Step 2: 3-[({4- [4- {4-[(methylcarbamoyl) amino] phenyl} -6- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) Preparation of -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 3-카르바모일페닐카르바메이트를 사용하여 제조하였다. 수득량 90 mg, 13％ 수율.The title compound was prepared according to the procedure of Example 462 step 7 in 1- (4- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl)- 1,3,5-triazin-2-yl) phenyl) -3-methylurea and phenyl 3-carbamoylphenylcarbamate. Yield 90 mg, 13% yield.

실시예: 466: 3-({[4-(4-{4-[(메틸카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드의 제조Example 466: 3-({[4- (4- {4-[(methylcarbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-triazine-2- Yl) phenyl] carbamoyl} amino) benzamide

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 3-카르바모일페닐카르바메이트를 사용하여 제조하였다. 수득량 51 mg, 4％ 수율.The title compound was converted to 1- (4- (4- (4-aminophenyl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 following the procedure of Example 462 step 7. Prepared using -methylurea and phenyl 3-carbamoylphenylcarbamate. Yield 51 mg, 4% yield.

실시예 467: 1-메틸-3-[4-(4-모르폴린-4-일-6-{4-[(피리딘-3-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)페닐]우레아의 제조Example 467: 1-methyl-3- [4- (4-morpholin-4-yl-6- {4-[(pyridin-3-ylcarbamoyl) amino] phenyl} -1,3,5- Preparation of Triazine-2-yl) phenyl] urea

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 피리딘-3-일카르바메이트를 사용하여 제조하였다. 수득량 77 mg, 6％ 수율.The title compound was converted to 1- (4- (4- (4-aminophenyl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 following the procedure of Example 462 step 7. Prepared using -methylurea and phenyl pyridin-3-ylcarbamate. Yield 77 mg, 6% yield.

실시예 468: 1-메틸-3-[4-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)페닐]우레아의 제조Example 468: 1-methyl-3- [4- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5- Preparation of Triazine-2-yl) phenyl] urea

단계 1: 페닐 피리딘-4-일카르바메이트의 제조Step 1: Preparation of Phenyl Pyridin-4-ylcarbamate

표제 화합물을 실시예 462 단계 6의 절차에 따라 4-아미노피리딘 및 페닐 클로로포르메이트를 사용하여 제조하였다. 수득량 6 g, 534％ 수율.The title compound was prepared using 4-aminopyridine and phenyl chloroformate following the procedure of Example 462 step 6. Yield 6 g, 534% yield.

단계 2: 1-메틸-3-[4-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)페닐]우레아의 제조Step 2: 1-methyl-3- [4- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-tri Preparation of Azin-2-yl) phenyl] urea

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 피리딘-4-일카르바메이트를 사용하여 제조하였다. 수득량 75 mg, 3.9％ 수율.The title compound was converted to 1- (4- (4- (4-aminophenyl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 following the procedure of Example 462 step 7. Prepared using -methylurea and phenyl pyridin-4-ylcarbamate. Yield 75 mg, 3.9% yield.

실시예 469: 3-[({4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조Example 469: 3-[({4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5 -Triazin-2-yl] phenyl} carbamoyl) amino] benzamide

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-(3,5-디메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 3-카르바모일페닐카르바메이트를 사용하여 제조하였다. 수득량 56 mg, 4.1％ 수율.The title compound was purified according to the procedure of Example 462 step 7, 1- (4- (4- (4-aminophenyl) -6- (3,5-dimethylmorpholino) -1,3,5-triazine-2 -Yl) phenyl) -3-methylurea and phenyl 3-carbamoylphenylcarbamate. Yield 56 mg, 4.1% yield.

실시예 470: 4-[({4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드의 제조Example 470: 4-[({4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5 -Triazin-2-yl] phenyl} carbamoyl) amino] benzamide

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-(3,5-디메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 4-카르바모일페닐카르바메이트를 사용하여 제조하였다. 수득량 70 mg, 12.8％ 수율.The title compound was purified according to the procedure of Example 462 step 7, 1- (4- (4- (4-aminophenyl) -6- (3,5-dimethylmorpholino) -1,3,5-triazine-2 -Yl) phenyl) -3-methylurea and phenyl 4-carbamoylphenylcarbamate. Yield 70 mg, 12.8% yield.

실시예 471: 1-메틸-3-{4-[4-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}우레아의 제조Example 471 1-methyl-3- {4- [4- (8-oxa-3-azabicyclo [3.2.1] oct-3-yl) -6- {4-[(pyridin-4-ylcar Preparation of barmoyl) amino] phenyl} -1,3,5-triazin-2-yl] phenyl} urea

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 피리딘-4-일카르바메이트를 사용하여 제조하였다. 수득량 51 mg, 4％ 수율.The title compound was prepared according to the procedure of Example 462 step 7 in 1- (4- (4- (4-aminophenyl) -6- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl)- 1,3,5-triazin-2-yl) phenyl) -3-methylurea and phenyl pyridin-4-ylcarbamate. Yield 51 mg, 4% yield.

실시예 472: 1-{4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아의 제조Example 472: 1- {4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-tri Preparation of Azin-2-yl] phenyl} -3-pyridin-4-ylurea

표제 화합물을 실시예 462 단계 7의 절차에 따라 1-(4-(4-(4-아미노페닐)-6-(3,5-디메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-메틸우레아 및 페닐 피리딘-4-일카르바메이트를 사용하여 제조하였다. 수득량 15 mg, 0.8％ 수율.The title compound was purified according to the procedure of Example 462 step 7, 1- (4- (4- (4-aminophenyl) -6- (3,5-dimethylmorpholino) -1,3,5-triazine-2 -Yl) phenyl) -3-methylurea and phenyl pyridin-4-ylcarbamate. Yield 15 mg, 0.8% yield.

실시예 473: N-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-2,2-디플루오로아세트아미드의 제조Example 473: Preparation of N- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -2,2-difluoroacetamide

단계 1: 4,4'-(6-클로로-1,3,5-트리아진-2,4-디일)디모르폴린의 제조Step 1: Preparation of 4,4 '-(6-Chloro-1,3,5-triazine-2,4-diyl) dimorpholine

메틸렌 100 mL 중 모르폴린 (8.71 g, 100 mmol)의 용액을 메틸렌 클로라이드 200 mL 중 시아누르산 클로라이드 (9.22 g, 50.0 mmol) 및 트리에틸아민 (10.1 g, 100 mmol)의 혼합물에 0℃에서 적가하였다. 이어서, 반응 혼합물을 0℃에서 1 시간 동안 교반하고, 실온까지 서서히 가온시켰다. 실온에서 1 시간 동안 교반한 후에, 반응 혼합물을 여과하여 트리에틸아민 히드로클로라이드 염을 제거하였다. 여과물을 농축시켜 4,4'-(6-클로로-1,3,5-트리아진-2,4-디일)디모르폴린 (14.2 g, 100 수율)을 백색 고체로서 수득하였다. HPLC: Rt = 2.43 분; MS 286, 288 [M+H].A solution of morpholine (8.71 g, 100 mmol) in 100 mL methylene was added dropwise at 0 ° C. to a mixture of cyanuric chloride (9.22 g, 50.0 mmol) and triethylamine (10.1 g, 100 mmol) in 200 mL methylene chloride. It was. The reaction mixture was then stirred at 0 ° C. for 1 hour and slowly warmed up to room temperature. After stirring for 1 hour at room temperature, the reaction mixture was filtered to remove triethylamine hydrochloride salt. The filtrate was concentrated to give 4,4 '-(6-chloro-1,3,5-triazine-2,4-diyl) dimorpholine (14.2 g, 100 yield) as a white solid. HPLC: Rt = 2.43 min; MS 286, 288 [M + H].

단계 2: 4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)아닐린의 제조Step 2: Preparation of 4- (4,6-dimorpholino-1,3,5-triazin-2-yl) aniline

2M 탄산나트륨 수용액 (10 mL, 20 mmol) 및 DME 40 mL 중 4,4'-(6-클로로-1,3,5-트리아진-2,4-디일)디모르폴린 (1.40 g, 4.90 mmol), 4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)아닐린 (2.62 g, 11.9 mmol) 및 테트라키스(트리페닐포스핀)팔라듐(0) (282 mg, 0.240 mmol)의 혼합물을 80℃에서 2 시간 동안 교반하였다. 반응 혼합물을 에틸 아세테이트 300 mL로 희석하고, 물로 세척하였다. 유기층을 농축시키고, 플래쉬 크로마토그래피 (ISCO, 120 g 실리카겔 컬럼, 0-100％ EtOAc/헥산으로 용리함)로 정제하여 4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)아닐린 (0.68 g, 40％ 수율)을 수득하였다. HPLC: Rt = 2.09 분; MS 343 [M+H].2M aqueous sodium carbonate solution (10 mL, 20 mmol) and 4,4 '-(6-chloro-1,3,5-triazine-2,4-diyl) dimorpholine (1.40 g, 4.90 mmol) in 40 mL of DME , 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (2.62 g, 11.9 mmol) and tetrakis (triphenylphosphine) palladium (0 ) (282 mg, 0.240 mmol) was stirred at 80 ° C. for 2 hours. The reaction mixture was diluted with 300 mL of ethyl acetate and washed with water. The organic layer was concentrated and purified by flash chromatography (ISCO, 120 g silica gel column, eluting with 0-100% EtOAc / hexanes) to 4- (4,6-dimorpholino-1,3,5-triazine 2-yl) aniline (0.68 g, 40% yield) was obtained. HPLC: R t = 2.09 min; MS 343 [M + H].

단계 3: N-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-2,2-디플루오로아세트아미드의 제조Step 3: Preparation of N- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -2,2-difluoroacetamide

DMF 2 mL 중 2,2-디플루오로아세트산 (20 mg, 0.21 mmol), HBTU (76 mg, 0.2 mmol) 및 DIEA (52 mg, 0.40 mmol)의 혼합물에 4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)아닐린 (40 mg, 0.12 mmol)을 첨가하였다. 반응물을 60℃에서 16 시간 동안 교반하였다. 이어서, 반응 혼합물을 실온으로 냉각시키고, 역상 크로마토그래피로 정제하여 N-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-2,2-디플루오로아세트아미드 (23 mg, 46％ 수율)을 수득하였다. HPLC: Rt = 2.19 분; MS 421 [M+H].4- (4,6-dimorpholi) in a mixture of 2,2-difluoroacetic acid (20 mg, 0.21 mmol), HBTU (76 mg, 0.2 mmol) and DIEA (52 mg, 0.40 mmol) in 2 mL of DMF. No-1,3,5-triazin-2-yl) aniline (40 mg, 0.12 mmol) was added. The reaction was stirred at 60 ° C. for 16 hours. The reaction mixture was then cooled to room temperature and purified by reverse phase chromatography to give N- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl]- 2,2-difluoroacetamide (23 mg, 46% yield) was obtained. HPLC: R t = 2.19 min; MS 421 [M + H].

실시예 474: N-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-4,5-디히드로-1H-이미다졸-2-아민의 제조Example 474: N- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -4,5-dihydro-1 H-imidazole- Preparation of 2-amines

DMF 2 mL 중 4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)아닐린 (40 mg, 0.12 mmol), 이미다졸리딘-2-티온 (15 mg, 0.15 mmol) 및 수은(II) 클로라이드 (40 mg, 0.15 mmol)의 혼합물을 140℃에서 16 시간 동안 교반하였다. 이어서, 반응 혼합물을 실온으로 냉각시키고, 셀라이트™를 통해 여과하였다. 여과물을 농축시키고, 역상 크로마토그래피로 정제하여 N-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-4,5-디히드로-1H-이미다졸-2-아민 (9.0 mg, 22％ 수율)을 수득하였다. HPLC: Rt = 1.74 분; MS 411 [M+H].4- (4,6-dimorpholino-1,3,5-triazin-2-yl) aniline (40 mg, 0.12 mmol), imidazolidine-2-thione (15 mg, in 2 mL of DMF 0.15 mmol) and mercury (II) chloride (40 mg, 0.15 mmol) were stirred at 140 ° C. for 16 h. The reaction mixture was then cooled to room temperature and filtered through Celite ™. The filtrate was concentrated and purified by reverse phase chromatography to give N- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -4,5- Dihydro-1H-imidazol-2-amine (9.0 mg, 22% yield) was obtained. HPLC: R t = 1.74 min; MS 411 [M + H].

실시예 475: 2,4-디모르폴린-4-일-6-[4-(2H-테트라졸-5-일)페닐]-1,3,5-트리아진의 제조Example 475: Preparation of 2,4-dimorpholin-4-yl-6- [4- (2H-tetrazol-5-yl) phenyl] -1,3,5-triazine

단계 1: 4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)벤조니트릴의 제조Step 1: Preparation of 4- (4,6-dimorpholino-1,3,5-triazin-2-yl) benzonitrile

표제 화합물을 실시예 473 단계 2의 절차에 따라 4,4'-(6-클로로-1,3,5-트리아진-2,4-디일)디모르폴린 및 4-시아노페닐-보론산을 사용하여 제조하였다. 수득량 86 mg, 50％ 수율; HPLC: Rt = 2.60 분; MS 353 [M+H].The title compound was purified using 4,4 ′-(6-chloro-1,3,5-triazine-2,4-diyl) dimorpholine and 4-cyanophenyl-boronic acid following the procedure of Example 473 step 2. Prepared using. Yield 86 mg, 50% yield; HPLC: R t = 2.60 min; MS 353 [M + H].

단계 2: 2,4-디모르폴린-4-일-6-[4-(2H-테트라졸-5-일)페닐]-1,3,5-트리아진의 제조Step 2: Preparation of 2,4-dimorpholin-4-yl-6- [4- (2H-tetrazol-5-yl) phenyl] -1,3,5-triazine

DMF 2 mL 중 4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)벤조니트릴 (11 mg, 0.031 mmol), 나트륨 아지드 (5.5 mg, 0.085 mmol) 및 트리에틸아민 히드로클로라이드 (6.0 mg, 0.043 mmol)의 혼합물을 120℃에서 6 시간 동안 교반하였다. 이어서, 반응 혼합물을 실온으로 냉각시키고, 역상 크로마토그래피로 정제하여 2,4-디모르폴린-4-일-6-[4-(2H-테트라졸-5-일)페닐]-1,3,5-트리아진을 수득하였다. 수득량 12 mg, 97％ 수율; HPLC: Rt = 2.09 분; MS 394 [M-H].4- (4,6-dimorpholino-1,3,5-triazin-2-yl) benzonitrile (11 mg, 0.031 mmol), sodium azide (5.5 mg, 0.085 mmol) in 2 mL DMF and A mixture of triethylamine hydrochloride (6.0 mg, 0.043 mmol) was stirred at 120 ° C. for 6 hours. The reaction mixture is then cooled to room temperature and purified by reverse phase chromatography to give 2,4-dimorpholin-4-yl-6- [4- (2H-tetrazol-5-yl) phenyl] -1,3, 5-triazine was obtained. Yield 12 mg, 97% yield; HPLC: R t = 2.09 min; MS 394 [M-H].

실시예 476: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-메틸우레아의 제조Example 476: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-methylurea

단계 1: 1-메틸-3-[4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보롤란-2-일)-페닐]-우레아의 제조Step 1: Preparation of 1-methyl-3- [4- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -phenyl] -urea

THF 50 mL 중 2-(4-이소시아네이토페닐)-4,4,5,5-테트라메틸-1,3,2-디옥사보롤란 (750 mg, 3.06 mmol), 2.0M 메틸아민/THF (2.3 mL, 4.60 mmol)의 혼합물을 실온에서 6 시간 동안 교반하였다. 이어서, 반응 혼합물을 농축시켜 1-메틸-3-[4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보롤란-2-일)-페닐]-우레아 (760 mg, 90％ 수율)를 수득하였다. Rt = 2.21 분; 277 [M+H].2- (4-isocyanatophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (750 mg, 3.06 mmol) in 50 mL THF, 2.0 M methylamine / A mixture of THF (2.3 mL, 4.60 mmol) was stirred at rt for 6 h. The reaction mixture is then concentrated to give 1-methyl-3- [4- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -phenyl] -urea ( 760 mg, 90% yield). Rt = 2.21 min; 277 [M + H].

단계 2: 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-메틸우레아의 제조Step 2: Preparation of 1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-methylurea

표제 화합물을 실시예 473 단계 2의 절차에 따라 4,4'-(6-클로로-1,3,5-트리아진-2,4-디일)디모르폴린 및 1-메틸-3-[4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보롤란-2-일)-페닐]-우레아를 사용하여 제조하였다. 수득량 13 mg, 11％ 수율; HPLC: Rt = 1.98 분; MS 400 [M+H].The title compound was prepared in accordance with the procedure of Example 473 step 2, 4,4 '-(6-chloro-1,3,5-triazine-2,4-diyl) dimorpholine and 1-methyl-3- [4- Prepared using (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -phenyl] -urea. Yield 13 mg, 11% yield; HPLC: R t = 1.98 min; MS 400 [M + H].

실시예 477: 2-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-N-피리딘-3-일아세트아미드의 제조Example 477 Preparation of 2- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -N-pyridin-3-ylacetamide

단계 1: 2-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)아세트산의 제조Step 1: Preparation of 2- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) acetic acid

2M 탄산나트륨 수용액 (3 mL, 8 mmol) 및 DME 20 mL 중 4,4'-(6-클로로-1,3,5-트리아진-2,4-디일)디모르폴린 (285 mg, 1.0 mmol), 2-(4-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)페닐)아세트산 (315 mg, 1.2 mmol) 및 테트라키스(트리페닐포스핀)팔라듐(0) (58 mg, 0.05 mmol)의 혼합물을 80℃에서 2 시간 동안 교반하였다. 이어서, 반응 혼합물을 에틸 아세테이트 50 mL로 희석하고, 1N NaOH (50 mL, 3회)로 추출하였다. 합한 수성층을 pH=6로 중성화시켰다. 이어서, 수용액을 에틸 아세테이트 (50 mL, 3회)로 추출하였다. 합한 유기층을 포화 탄산나트륨 및 염수로 세척하였다. 이어서, 유기층을 무수 황산나트륨 상에서 건조시키고 농축시켜 2-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)아세트산 (68 mg, 18％ 수율)을 수득하였다. HPLC: Rt = 2.04 분; MS 386 [M+H].2M aqueous sodium carbonate solution (3 mL, 8 mmol) and 4,4 '-(6-chloro-1,3,5-triazine-2,4-diyl) dimorpholine (285 mg, 1.0 mmol) in 20 mL of DME , 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) acetic acid (315 mg, 1.2 mmol) and tetrakis (triphenylforce) Pin) palladium (0) (58 mg, 0.05 mmol) was stirred at 80 ° C. for 2 h. The reaction mixture was then diluted with 50 mL of ethyl acetate and extracted with 1N NaOH (50 mL, 3 times). The combined aqueous layers were neutralized to pH = 6. The aqueous solution was then extracted with ethyl acetate (50 mL, 3 times). The combined organic layers were washed with saturated sodium carbonate and brine. The organic layer was then dried over anhydrous sodium sulfate and concentrated to 2- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) acetic acid (68 mg, 18% yield) Obtained. HPLC: R t = 2.04 min; MS 386 [M + H].

단계 2: 2-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-N-피리딘-3-일아세트아미드의 제조Step 2: Preparation of 2- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -N-pyridin-3-ylacetamide

표제 화합물을 실시예 473 단계 3의 절차에 따라 2-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)아세트산 및 3-아미노피리딘을 사용하여 제조하였다. 수득량 21 mg, 44％ 수율; HPLC: Rt = 1.91 분; MS 462 [M+H].The title compound was used 2- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) acetic acid and 3-aminopyridine following the procedure of Example 473 step 3 It was prepared by. Yield 21 mg, 44% yield; HPLC: R t = 1.91 min; MS 462 [M + H].

((2S,5R)-1-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)피롤리딘-2,5-디일)디메탄올의 제조((2S, 5R) -1- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-nitrophenyl) -1,3,5-triazine Preparation of 2-yl) pyrrolidin-2,5-diyl) dimethanol

에탄올 (15 mL) 중 ((2S,5R)-1-(4-클로로-6-(4-니트로페닐)-1,3,5-트리아진-2-일)피롤리딘-2,5-디일)디메탄올 (1.3 g, 2.7 mmol), 8-옥사-3-아자비시클로[3.2.1]옥탄 히드로클로라이드 (0.51 g, 3.4 mmol)의 현탁액을 트리에틸아민 (1.35 mL, 10 mmol)으로 처리하고, 힛건을 이용하여 간단하게 환류로 가열하였다. 반응 혼합물을 자동화 플래쉬 크로마토그래피 (메탄올/클로로포름)로 정제하여 표제 화합물을 경질 복숭아색 발포체로서 수득하였다. MS (ES+) = 443.2 (M+H)+ ((2S, 5R) -1- (4-chloro-6- (4-nitrophenyl) -1,3,5-triazin-2-yl) pyrrolidine-2,5- in ethanol (15 mL) Treatment of a suspension of diyl) dimethanol (1.3 g, 2.7 mmol), 8-oxa-3-azabicyclo [3.2.1] octane hydrochloride (0.51 g, 3.4 mmol) with triethylamine (1.35 mL, 10 mmol) And it heated simply to reflux using the gun. The reaction mixture was purified by automated flash chromatography (methanol / chloroform) to afford the title compound as a light peach foam. MS (ES + ) = 443.2 (M + H) +

3-(4-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄의 제조3- (4-((2S, 5R) -2,5-bis ((tert-butyldimethylsilyloxy) methyl) pyrrolidin-1-yl) -6- (4-nitrophenyl) -1,3, Preparation of 5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane

디클로로메탄 (15 mL) 중 ((2S,5R)-1-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)피롤리딘-2,5-디일)디메탄올 (1.5 g, 3.4 mmol)의 용액을 tert-부틸 디메틸 클로로실란 (1.3 g, 8.5 mmol) 및 이미다졸 (0.69 g, 10 mmol)로 순서대로 처리하였다. 생성된 현탁액을 실온에서 밤새 교반한 다음, 물로 켄칭하였다. 수성상을 디클로로메탄으로 3회 추출하였다. 합한 추출물을 무수 황산마그네슘 상에서 건조시키고, 여과하고, 감압하에 농축시켜 건조시켰다. 조 잔류물 (복숭아색 고체)를 다음 단계에 추가 정제 없이 사용하였다. MS (ES+) = 671.4 (M+H)+ ((2S, 5R) -1- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6- (4-nitrophenyl) -1 in dichloromethane (15 mL) A solution of, 3,5-triazin-2-yl) pyrrolidine-2,5-diyl) dimethanol (1.5 g, 3.4 mmol) was added to tert-butyl dimethyl chlorosilane (1.3 g, 8.5 mmol) and imidazole. (0.69 g, 10 mmol) were treated sequentially. The resulting suspension was stirred at rt overnight and then quenched with water. The aqueous phase was extracted three times with dichloromethane. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The crude residue (peach solid) was used in the next step without further purification. MS (ES + ) = 671.4 (M + H) +

4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-1,3,5-트리아진-2-일)아닐린의 제조4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-((2S, 5R) -2,5-bis ((tert-butyldimethylsilyloxy) methyl Preparation of Pyrrolidin-1-yl) -1,3,5-triazin-2-yl) aniline

테트라히드로푸란 (30 mL) 중 차콜 상 팔라듐 (10％, 100 mg) 및 조 3-(4-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-6-(4-니트로페닐)-1,3,5-트리아진-2-일)-8-옥사-3-아자비시클로[3.2.1]옥탄 (최대 3.4 mmol)의 현탁액을 8 시간 동안 수소 50 psi 하에 진탕시켰다. 혼합물을 셀라이트™ 규조토 패드를 통해 여과하고, 감압하에 농축시켜 표제 화합물을 오렌지색 발포체로서 수득하였다. MS (ES+) = 642.4 (M+H)+ Palladium on charcoal (10%, 100 mg) and crude 3- (4-((2S, 5R) -2,5-bis ((tert-butyldimethylsilyloxy) methyl) pyrroli in tetrahydrofuran (30 mL) Din-1-yl) -6- (4-nitrophenyl) -1,3,5-triazin-2-yl) -8-oxa-3-azabicyclo [3.2.1] octane (up to 3.4 mmol) The suspension was shaken under 50 psi of hydrogen for 8 hours. The mixture was filtered through a pad of Celite ™ diatomaceous earth and concentrated under reduced pressure to afford the title compound as an orange foam. MS (ES + ) = 642.4 (M + H) +

실시예 667: 1-(4-{4-[(2R,5S)-2,5-비스(히드록시메틸)피롤리딘-1-일]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아의 제조Example 667: 1- (4- {4-[(2R, 5S) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl] -6- (8-oxa-3-azabicyclo [ 3.2.1] Oct-3-yl) -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea

디클로로메탄 (5 mL) 중 4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-1,3,5-트리아진-2-일)아닐린 (0.24 g, 0.37 mmol)의 용액을 트리에틸아민 (500 μL), 및 디클로로메탄 (1 mL) 중 트리포스겐 (56 mg) 용액으로 순서대로 처리하였다. 5 분 후에, 혼합물을 따뜻한 테트라히드로푸란 중 4-아미노피리딘 (70 mg)의 용액으로 처리하였다. 1 시간 후, 반응 혼합물을 메탄올로 켄칭하고, 농축시켜 건조시켰다. 조 잔류물의 절반을 메탄올 중 포화 염화수소 용액으로 처리하였다. 탈실릴화 완료에 따라, 혼합물을 농축시켜 건조시키고, 잔류물을 25 분에 걸쳐 5％ 아세토니트릴/95％의 0.1％ 수성 트리플루오로아세트산에서 50％ 아세토니트릴의 구배 용리로 진행하는 페노메넥스 프로디지 컬럼을 사용하는 역상 고성능 액체 크로마토그래피로 정제하였다. 농축 후, 표제 화합물을 그의 트리플루오로아세트산 염으로서 수득하였다 (75 mg). MS (ES+) = 533.3 (M+H)+ 4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-((2S, 5R) -2,5-bis ((tert) in dichloromethane (5 mL) A solution of -butyldimethylsilyloxy) methyl) pyrrolidin-1-yl) -1,3,5-triazin-2-yl) aniline (0.24 g, 0.37 mmol) in triethylamine (500 μL), and Treated sequentially with a solution of triphosgen (56 mg) in dichloromethane (1 mL). After 5 minutes, the mixture was treated with a solution of 4-aminopyridine (70 mg) in warm tetrahydrofuran. After 1 h, the reaction mixture was quenched with methanol, concentrated to dryness. Half of the crude residue was treated with saturated hydrogen chloride solution in methanol. Upon completion of desilylation, the mixture was concentrated to dryness and the residue proceeded to a gradient elution of 50% acetonitrile in 5% acetonitrile / 95% 0.1% aqueous trifluoroacetic acid over 25 minutes. Purification by reverse phase high performance liquid chromatography using a Prodigy column. After concentration, the title compound was obtained as its trifluoroacetic acid salt (75 mg). MS (ES + ) = 533.3 (M + H) +

실시예 668: 1-(4-{4-[(2R,5S)-2,5-비스(히드록시메틸)피롤리딘-1-일]-6-(8-옥사-3-아자비시클로[3.2.1]옥트-3-일)-1,3,5-트리아진-2-일}페닐)-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조Example 668: 1- (4- {4-[(2R, 5S) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl] -6- (8-oxa-3-azabicyclo [ 3.2.1] Oct-3-yl) -1,3,5-triazin-2-yl} phenyl) -3- [4- (4-methylpiperazin-1-yl) phenyl] urea

디클로로메탄 (5 mL) 중 4-(4-(8-옥사-3-아자비시클로[3.2.1]옥탄-3-일)-6-((2S,5R)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-일)-1,3,5-트리아진-2-일)아닐린 (0.25 g, 0.39 mmol)의 용액을 트리에틸아민 (500 μL), 및 디클로로메탄 (1 mL) 중 트리포스겐 (59 mg, 0.08 mmol) 용액으로 순서대로 처리하였다. 5 분 후에, 혼합물을 4-(4-메틸피페라진-1-일)아닐린 (150 mg)으로 처리하였다. 1 시간 후, 반응 혼합물을 메탄올로 켄칭하고, 농축시켜 건조시켰다. 조 잔류물을 메탄올 중 포화 염화수소 용액으로 처리하였다. 탈실릴화 완료에 따라, 혼합물을 농축시켜 건조시키고, 잔류물을 15 분에 걸쳐 5％ 아세토니트릴/55％의 0.1％ 수성 트리플루오로아세트산에서 50％ 아세토니트릴의 구배 용리로 진행하는 페노메넥스 게미니(Phenomenex Gemini) 컬럼을 사용하여 역상 고성능 액체 크로마토그래피로 정제하였다. 농축 후, 표제 화합물을 그의 트리플루오로아세트산 염으로서 수득하였다 (130 mg). MS (ES+) = 630.4 (M+H)+ 4- (4- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -6-((2S, 5R) -2,5-bis ((tert) in dichloromethane (5 mL) A solution of -butyldimethylsilyloxy) methyl) pyrrolidin-1-yl) -1,3,5-triazin-2-yl) aniline (0.25 g, 0.39 mmol) in triethylamine (500 μL), and Treated sequentially with a solution of triphosgen (59 mg, 0.08 mmol) in dichloromethane (1 mL). After 5 minutes, the mixture was treated with 4- (4-methylpiperazin-1-yl) aniline (150 mg). After 1 h, the reaction mixture was quenched with methanol, concentrated to dryness. The crude residue was treated with saturated hydrogen chloride solution in methanol. Upon completion of desilylation, the mixture was concentrated to dryness and the residue proceeded to a gradient elution of 50% acetonitrile in 5% acetonitrile / 55% 0.1% aqueous trifluoroacetic acid over 15 minutes. Purification by reverse phase high performance liquid chromatography using a Phenomenex Gemini column. After concentration, the title compound was obtained as its trifluoroacetic acid salt (130 mg). MS (ES + ) = 630.4 (M + H) +

실시예 823: 1-[4-(4,6-디-3,7-디옥사-9-아자비시클로[3.3.1]논-9-일-1,3,5-트리아진-2-일)페닐]-3-[4-(4-메틸피페라진-1-일)페닐]우레아의 제조Example 823 1- [4- (4,6-di-3,7-dioxa-9-azabicyclo [3.3.1] non-9-yl-1,3,5-triazin-2-yl ) Phenyl] -3- [4- (4-methylpiperazin-1-yl) phenyl] urea

CH2Cl2 (20 mL) 중 시아누르산 클로라이드 (0.368 g, 2 mmol)의 용액에 3,7-디옥사-9-아자비시클로[3.3.1]노난을 첨가하였다. HCO2H (0.718 g, 4.1 mmol)에 이어 Et3N (0.98 mL, 7 mmol)을 첨가하였다. 생성된 반응 혼합물을 24 시간 동안 교반한 다음, CH2Cl2로 희석하였다. 유기상을 수성 1N HCl (3X)로 세척하고, MgSO4 상에서 건조시켰다. 용매를 진공 하에 제거하여 9,9'-(6-클로로-1,3,5-트리아진-2,4-디일)비스(3,7-디옥사-9-아자비시클로[3.3.1]노난)을 백색 고체로서 수득하였다 (0.15 g, 95％ 수율).To a solution of cyanuric chloride (0.368 g, 2 mmol) in CH 2 Cl 2 (20 mL) was added 3,7-dioxa-9-azabicyclo [3.3.1] nonane. HCO 2 H (0.718 g, 4.1 mmol) was added followed by Et 3 N (0.98 mL, 7 mmol). The resulting reaction mixture was stirred for 24 hours and then diluted with CH 2 Cl 2 . The organic phase was washed with aqueous 1N HCl (3X) and dried over MgSO 4 . The solvent was removed in vacuo to give 9,9 '-(6-chloro-1,3,5-triazine-2,4-diyl) bis (3,7-dioxa-9-azabicyclo [3.3.1] nonane ) Was obtained as a white solid (0.15 g, 95% yield).

10 mL 바이알에 9,9'-(6-클로로-1,3,5-트리아진-2,4-디일)비스(3,7-디옥사-9-아자비시클로[3.3.1]노난) (150 mg, 0.406 mmol), 4-아미노페닐보론산 피나콜 에스테르 (133 mg, 0.61 mmol), Pd(PPh3)4 (10 mg), 톨루엔 (1 mL), EtOH (1 mL) 및 2M Na2CO3 수용액 (0.305 mL)을 첨가하였다. 생성된 혼합물을 120℃에서 20 분 동안 마이크로파 오븐에서 가열하였다. 반응 혼합물을 실온으로 냉각시켰다. 수성상을 EtOAc로 추출하고, 합한 유기상을 건조시켰다 (MgSO4). 용매를 감압하에 제거하고, 잔류물을 HPLC 분리에 적용하여 4-(4,6-디(3,7-디옥사-9-아자비시클로[3.3.1]노난-9-일)-1,3,5-트리아진-2-일)아닐린을 백색 고체로서 수득하였다 (120 mg).9,9 '-(6-chloro-1,3,5-triazine-2,4-diyl) bis (3,7-dioxa-9-azabicyclo [3.3.1] nonane) in a 10 mL vial ( 150 mg, 0.406 mmol), 4-aminophenylboronic acid pinacol ester (133 mg, 0.61 mmol), Pd (PPh 3 ) 4 (10 mg), toluene (1 mL), EtOH (1 mL) and 2M Na 2 CO 3 aqueous solution (0.305 mL) was added. The resulting mixture was heated in a microwave oven at 120 ° C. for 20 minutes. The reaction mixture was cooled to room temperature. The aqueous phase was extracted with EtOAc and the combined organic phases were dried (MgSO 4 ). The solvent was removed under reduced pressure and the residue was subjected to HPLC separation to afford 4- (4,6-di (3,7-dioxa-9-azabicyclo [3.3.1] nonan-9-yl) -1,3 , 5-triazin-2-yl) aniline was obtained as a white solid (120 mg).

CH2Cl2 중 4-(4,6-디(3,7-디옥사-9-아자비시클로[3.3.1]노난-9-일)-1,3,5-트리아진-2-일)아닐린 (120 mg, 0.281 mmol)의 용액에 Et3N (0.237 mL, 1.69 mmol) 및 트리포스겐 (42 mg, 0.14 mmol)을 첨가하였다. 혼합물을 실온에서 15 분 동안 교반하고, 4-(4-메틸피페라진-1-일)아닐린 (107 mg, 0.56 mmol)을 첨가하였다. 혼합물을 실온에서 밤새 교반하였다. 용매를 제거하고, 잔류물을 HPLC 분리에 적용하여 표제 화합물 (1TFA 염)을 수득하였다. MS(ESI) m/z 644.3306.4- (4,6-di (3,7-dioxa-9-azabicyclo [3.3.1] nonan-9-yl) -1,3,5-triazin-2-yl) in CH 2 Cl 2 ) To a solution of aniline (120 mg, 0.281 mmol) was added Et 3 N (0.237 mL, 1.69 mmol) and triphosgene (42 mg, 0.14 mmol). The mixture was stirred at rt for 15 min and 4- (4-methylpiperazin-1-yl) aniline (107 mg, 0.56 mmol) was added. The mixture was stirred at room temperature overnight. Solvent was removed and the residue was subjected to HPLC fractions to afford the title compound (1TFA salt). MS (ESI) m / z 644.3306.

(6S)-tert-부틸 6-히드록시-3-옥사-8-아자비시클로[3.2.1]옥탄-8-카르복실레이트의 제조 (반응식 10)Preparation of (6S) -tert-butyl 6-hydroxy-3-oxa-8-azabicyclo [3.2.1] octane-8-carboxylate (Scheme 10)

단계 1: (2R',5S')-1-tert-부틸 2,5-디메틸 1H-피롤-1,2,5(2H,5H)-트리카르복실레이트 (시스-디에스테르)를 문헌 [Organic Letters 2004, 6(18), 3055-8]에 기재된 절차에 따라 합성하였다.Step 1: (2R ', 5S')-1-tert-butyl 2,5-dimethyl 1H-pyrrole-1,2,5 (2H, 5H) -tricarboxylate (cis-diester) is described in [Organic] Letters 2004, 6 (18), 3055-8].

단계 2: 시스-디에스테르의 (2R',5S')-tert-부틸 2,5-비스(히드록시메틸)-2,5-디히드로-1H-피롤-1-카르복실레이트 (시스-디올)로의 환원Step 2: (2R ', 5S')-tert-butyl 2,5-bis (hydroxymethyl) -2,5-dihydro-1H-pyrrole-1-carboxylate (cis-diol) of cis-diester Reduction to

THF (100 mL) 중 (2R',5S')-1-tert-부틸 2,5-디메틸 1H-피롤-1,2,5(2H,5H)-트리카르복실레이트 (6.6 g, 23.1 mmol)의 용액에 LiBH4 용액 (THF 중 2M, 34.7 mL, 69.4 mmol)을 0℃에서 서서히 첨가하였다. 생성된 혼합물을 실온에서 3 시간 동안 교반한 후에, 0℃로 다시 냉각시켰다. HCl 용액 (1M, 30 mL)을 반응 혼합물에 첨가하고, 10 분 동안 교반한 후에, EtOAc로 희석하였다. 유기층을 분리하고, 수성상을 EtOAc로 추출하였다. 합한 유기상을 물 및 염수로 세척하고 건조시켰다 (MgSO4). 유기 용매를 진공하에 제거하여 조 생성물을 얻고, 이를 EtOAc:Hex:MeOH (50:50:10)를 사용하는 실리카겔 플래쉬 크로마토그래피로 정제하여 시스-디올을 수득하였다 (3.8 g, 72％).(2R ', 5S')-1-tert-butyl 2,5-dimethyl 1H-pyrrole-1,2,5 (2H, 5H) -tricarboxylate (6.6 g, 23.1 mmol) in THF (100 mL) To the solution of LiBH 4 solution (2M in THF, 34.7 mL, 69.4 mmol) was added slowly at 0 ° C. The resulting mixture was stirred at rt for 3 h and then cooled back to 0 ° C. HCl solution (1M, 30 mL) was added to the reaction mixture, stirred for 10 minutes and then diluted with EtOAc. The organic layer was separated and the aqueous phase extracted with EtOAc. The combined organic phases were washed with water and brine and dried (MgSO 4 ). The organic solvent was removed in vacuo to afford the crude product, which was purified by silica gel flash chromatography using EtOAc: Hex: MeOH (50:50:10) to give cis-diol (3.8 g, 72%).

단계 3: (2R',5S')-tert-부틸 2,5-비스((tert-부틸디메틸실릴옥시)메틸)-2,5-디히드로-1H-피롤-1-카르복실레이트의 제조Step 3: Preparation of (2R ', 5S')-tert-butyl 2,5-bis ((tert-butyldimethylsilyloxy) methyl) -2,5-dihydro-1H-pyrrole-1-carboxylate

DMF (15 mL) 중 시스-디올 (3.57 g, 15.6 mmol)의 용액에 TBSCl (5.16 g, 34.3 mmol) 및 이미다졸 (3.18 g, 46.7 mmol)을 첨가하였다. 혼합물을 80℃에서 30 분 동안 마이크로파 오븐에서 (150 watt) 가열하였다. 실온으로 냉각시키고, 혼합물을 물 (50 mL) 및 EtOAc (50 mL) 중에 녹였다. 유기층을 분리하고, 수성상을 EtOAc로 추출하였다. 합한 유기상을 물 및 염수로 세척하고, 건조시켰다 (MgSO4). 유기 용매를 진공하에 제거하여 조 생성물을 얻고, 이를 EtOAc:Hex (10:90)을 사용하는 실리카겔 플래쉬 크로마토그래피로 정제하여 표제 화합물을 수득하였다 (7.12 g, 98％).To a solution of cis-diol (3.57 g, 15.6 mmol) in DMF (15 mL) was added TBSCl (5.16 g, 34.3 mmol) and imidazole (3.18 g, 46.7 mmol). The mixture was heated at 80 ° C. for 30 minutes in a microwave oven (150 watt). Cool to room temperature and dissolve the mixture in water (50 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous phase extracted with EtOAc. The combined organic phases were washed with water and brine and dried (MgSO 4 ). The organic solvent was removed in vacuo to afford the crude product, which was purified by silica gel flash chromatography using EtOAc: Hex (10:90) to give the title compound (7.12 g, 98%).

단계 4: (2R',3S',5R')-tert-부틸 2,5-비스((tert-부틸디메틸실릴옥시)메틸)-3-히드록시피롤리딘-1-카르복실레이트 (트랜스-알콜)의 합성Step 4: (2R ', 3S', 5R ')-tert-butyl 2,5-bis ((tert-butyldimethylsilyloxy) methyl) -3-hydroxypyrrolidine-1-carboxylate (trans- Synthesis of Alcohol)

THF (50 mL) 중 (2R',5S')-tert-부틸 2,5-비스((tert-부틸디메틸실릴옥시)메틸)-2,5-디히드로-1H-피롤-1-카르복실레이트 (4.8 g, 10.5 mmol)의 용액에 BH3 DMS 용액 (THF 중 2M, 6.97 mL, 13.9 mmol)을 0℃에서 서서히 첨가하였다. 생성된 혼합물을 실온에서 3 시간 동안 교반한 후에, 0℃로 다시 냉각시켰다. NaOH 용액 (5M, 12.6 mL, 63.2 mmol)을 반응 혼합물에 첨가한 다음, H2O2 (30％, 6.33 mL, 62.0 mmol)를 첨가하였다. 생성된 혼합물을 5 시간 동안 교반한 후에, EtOAc로 희석하였다. 유기층을 분리하고, 수성상을 EtOAc로 추출하였다. 합한 유기상을 물 및 염수로 세척하고, 건조시켰다 (MgSO4). 유기 용매를 진공하에 제거하여 조 생성물을 얻고, 이를 EtOAc:Hex (30:70)를 사용하는 실리카겔 플래쉬 크로마토그래피로 정제하여 표제 화합물을 수득하였다 (3.8 g, 77％).(2R ', 5S')-tert-butyl 2,5-bis ((tert-butyldimethylsilyloxy) methyl) -2,5-dihydro-1H-pyrrole-1-carboxylate in THF (50 mL) To a solution of (4.8 g, 10.5 mmol) BH 3 DMS solution (2M in THF, 6.97 mL, 13.9 mmol) was added slowly at 0 ° C. The resulting mixture was stirred at rt for 3 h and then cooled back to 0 ° C. NaOH solution (5M, 12.6 mL, 63.2 mmol) was added to the reaction mixture, followed by H 2 O 2 (30%, 6.33 mL, 62.0 mmol). The resulting mixture was stirred for 5 hours and then diluted with EtOAc. The organic layer was separated and the aqueous phase extracted with EtOAc. The combined organic phases were washed with water and brine and dried (MgSO 4 ). The organic solvent was removed in vacuo to afford the crude product, which was purified by silica gel flash chromatography using EtOAc: Hex (30:70) to give the title compound (3.8 g, 77%).

단계 5: 트랜스 알콜의 벤질 보호Step 5: Benzyl Protection of Trans Alcohols

THF (50 mL) 중 (2R',3S',5R')-tert-부틸 2,5-비스((tert-부틸디메틸실릴옥시)메틸)-3-히드록시피롤리딘-1-카르복실레이트 (2.515 g, 5.3 mmol)의 용액에 NaH (60％, 0.423 g, 10.6 mmol)를 첨가하였다. 혼합물을 실온에서 30 분 동안 교반하고, 벤질 브로마이드 (1.085 g, 6.3 mmol) 및 TBAI (0.195 g, 0.5 mmol)를 첨가하였다. 혼합물을 실온에서 12 시간 동안 교반하고, 포화 NH4Cl 용액 (20 mL)을 첨가하여 켄칭하였다. 진공하에 농축시키고, 잔류물을 물 및 EtOAc 중에 용해시켰다. 유기층을 분리하고, 수성상을 EtOAc로 추출하였다. 합한 유기상을 물 및 염수로 세척하고, 건조시켰다 (MgSO4). 유기 용매를 진공하에 제거하여 조 생성물을 얻고, 이를 EtOAc:Hex (10:90)를 사용하는 실리카겔 플래쉬 크로마토그래피로 정제하여 (2R',3S',5R')-tert-부틸 3-(벤질옥시)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-카르복실레이트 (3.0 g, 100％)를 무색 오일로서 수득하였다.(2R ', 3S', 5R ')-tert-butyl 2,5-bis ((tert-butyldimethylsilyloxy) methyl) -3-hydroxypyrrolidine-1-carboxylate in THF (50 mL) To a solution of (2.515 g, 5.3 mmol) was added NaH (60%, 0.423 g, 10.6 mmol). The mixture was stirred at rt for 30 min and benzyl bromide (1.085 g, 6.3 mmol) and TBAI (0.195 g, 0.5 mmol) were added. The mixture was stirred at rt for 12 h and quenched by addition of saturated NH 4 Cl solution (20 mL). Concentrated in vacuo and the residue was dissolved in water and EtOAc. The organic layer was separated and the aqueous phase extracted with EtOAc. The combined organic phases were washed with water and brine and dried (MgSO 4 ). The organic solvent was removed in vacuo to afford the crude product, which was purified by silica gel flash chromatography using EtOAc: Hex (10:90) to give (2R ', 3S', 5R ')-tert-butyl 3- (benzyloxy ) -2,5-bis ((tert-butyldimethylsilyloxy) methyl) pyrrolidine-1-carboxylate (3.0 g, 100%) was obtained as a colorless oil.

단계 6: (2R',3S',5R')-tert-부틸 3-(벤질옥시)-2,5-비스(히드록시메틸)피롤리딘-1-카르복실레이트 (벤질옥시 디올)의 합성Step 6: Synthesis of (2R ', 3S', 5R ')-tert-butyl 3- (benzyloxy) -2,5-bis (hydroxymethyl) pyrrolidine-1-carboxylate (benzyloxy diol)

THF (50 mL) 중 (2R',3S',5R')-tert-부틸 3-(벤질옥시)-2,5-비스((tert-부틸디메틸실릴옥시)메틸)피롤리딘-1-카르복실레이트 (3.0 g, 5.3 mmol)의 용액에 TBAF 용액 (THF 중 1M, 21.8 mL, 21.8 mmol)을 0℃에서 서서히 첨가하였다. 생성된 혼합물을 실온에서 6 동안 교반하고, 포화 NH4Cl 용액 (10 mL)을 첨가하여 켄칭하였다. 진공하에 농축시키고, 잔류물을 물 및 EtOAc로 처리하였다. 유기층을 분리하고, 수성상을 EtOAc로 추출하였다. 합한 유기상을 물 및 염수로 세척하고, 건조시켰다 (MgSO4). 유기 용매를 진공하에 제거하여 조 생성물을 얻고, 이를 EtOAc:Hex:MeOH (50:50:5)를 사용하는 실리카겔 플래쉬 크로마토그래피로 정제하여 표제 화합물을 수득하였다 (1.15 g, 62.5％).(2R ', 3S', 5R ')-tert-butyl 3- (benzyloxy) -2,5-bis ((tert-butyldimethylsilyloxy) methyl) pyrrolidine-1-carthol in THF (50 mL) To a solution of carboxylate (3.0 g, 5.3 mmol) TBAF solution (1M in THF, 21.8 mL, 21.8 mmol) was added slowly at 0 ° C. The resulting mixture was stirred at rt for 6 and quenched by addition of saturated NH 4 Cl solution (10 mL). Concentrated in vacuo and the residue was treated with water and EtOAc. The organic layer was separated and the aqueous phase extracted with EtOAc. The combined organic phases were washed with water and brine and dried (MgSO 4 ). The organic solvent was removed in vacuo to afford the crude product, which was purified by silica gel flash chromatography using EtOAc: Hex: MeOH (50: 50: 5) to give the title compound (1.15 g, 62.5%).

단계 7: 고리화에 의한 (6S')-tert-부틸 6-(벤질옥시)-3-옥사-8-아자비시클로[3.2.1]옥탄-8-카르복실레이트의 합성Step 7: Synthesis of (6S ')-tert-butyl 6- (benzyloxy) -3-oxa-8-azabicyclo [3.2.1] octane-8-carboxylate by cyclization

THF (50 mL) 중 (2R',3S',5R')-tert-부틸 3-(벤질옥시)-2,5-비스(히드록시메틸)피롤리딘-1-카르복실레이트 (1.15 g, 3.4 mmol)의 용액에 NaH (60％, 0.409 g, 10.2 mmol)를 첨가하였다. 혼합물을 실온에서 30 분 동안 교반하고, 0℃로 냉각시켰다. THF (5 mL) 중 p-TsCl (0.65 g, 3.4 mmol)의 용액을 서서히 혼합물에 첨가하였다. 이어서, 반응 혼합물을 실온에서 12 시간 동안 교반하고, 포화 NH4Cl 용액 (20 mL)을 첨가하여 켄칭하였다. 진공하에 농축시키고, 잔류물을 물 및 EtOAc 중에 녹였다. 유기층을 분리하고, 수성상을 EtOAc로 추출하였다. 합한 유기상을 물 및 염수로 세척하고, 건조시켰다 (MgSO4). 유기 용매를 진공하에 제거하여 조 생성물을 얻고, 이를 EtOAc:Hex (20:80)를 사용하는 실리카겔 플래쉬 크로마토그래피로 정제하여 표제 화합물 (716 mg, 66％)을 회백색 고체로서 수득하였다.(2R ', 3S', 5R ')-tert-butyl 3- (benzyloxy) -2,5-bis (hydroxymethyl) pyrrolidine-1-carboxylate (1.15 g, in THF (50 mL), 3.4 mmol) was added NaH (60%, 0.409 g, 10.2 mmol). The mixture was stirred at room temperature for 30 minutes and cooled to 0 &lt; 0 &gt; C. A solution of p-TsCl (0.65 g, 3.4 mmol) in THF (5 mL) was slowly added to the mixture. The reaction mixture was then stirred at rt for 12 h and quenched by addition of saturated NH 4 Cl solution (20 mL). Concentrated in vacuo and the residue was taken up in water and EtOAc. The organic layer was separated and the aqueous phase extracted with EtOAc. The combined organic phases were washed with water and brine and dried (MgSO 4 ). The organic solvent was removed in vacuo to afford the crude product, which was purified by silica gel flash chromatography using EtOAc: Hex (20:80) to afford the title compound (716 mg, 66%) as off-white solid.

표 I의 화합물은 상기 방법에 따라 제조하였다.The compounds of Table I were prepared according to the above method.

<표 I><Table I>

Figure 112010076169004-pct00075
Figure 112010076169004-pct00075

Figure 112010076169004-pct00076
Figure 112010076169004-pct00076

Figure 112010076169004-pct00077
Figure 112010076169004-pct00077

Figure 112010076169004-pct00078
Figure 112010076169004-pct00078

Figure 112010076169004-pct00079
Figure 112010076169004-pct00079

Figure 112010076169004-pct00080
Figure 112010076169004-pct00080

Figure 112010076169004-pct00081
Figure 112010076169004-pct00081

Figure 112010076169004-pct00082
Figure 112010076169004-pct00082

Figure 112010076169004-pct00083
Figure 112010076169004-pct00083

Figure 112010076169004-pct00084
Figure 112010076169004-pct00084

Figure 112010076169004-pct00085
Figure 112010076169004-pct00085

Figure 112010076169004-pct00086
Figure 112010076169004-pct00086

Figure 112010076169004-pct00087
Figure 112010076169004-pct00087

Figure 112010076169004-pct00088
Figure 112010076169004-pct00088

Figure 112010076169004-pct00089
Figure 112010076169004-pct00089

Figure 112010076169004-pct00090
Figure 112010076169004-pct00090

Figure 112010076169004-pct00091
Figure 112010076169004-pct00091

Figure 112010076169004-pct00092
Figure 112010076169004-pct00092

Figure 112010076169004-pct00093
Figure 112010076169004-pct00093

Figure 112010076169004-pct00094
Figure 112010076169004-pct00094

Figure 112010076169004-pct00095
Figure 112010076169004-pct00095

Figure 112010076169004-pct00096
Figure 112010076169004-pct00096

Figure 112010076169004-pct00097
Figure 112010076169004-pct00097

Figure 112010076169004-pct00098
Figure 112010076169004-pct00098

Figure 112010076169004-pct00099
Figure 112010076169004-pct00099

Figure 112010076169004-pct00100
Figure 112010076169004-pct00100

생물학적 평가Biological evaluation

mTOR 키나제 검정 방법mTOR kinase assay method

정제된 효소를 사용하는 인간 mTOR 검정 (문헌 [Toral-Barza, et al. Biochem Biophys. Res. Commun. 2005 June 24;332(1):304-10] 참조)은 다음과 같이 델피아(DELFIA) 포맷에 따라 96-웰 플레이트에서 수행하였다. 먼저, 효소를 키나제 검정 완충액 (10 mM HEPES (pH 7.4), 50 mM NaCl, 50 mM β-글리세로포스페이트, 10 mM MnCl2, 0.5 mM DTT, 0.25 mM 마이크로시스틴 LR 및 100 mg/ml BSA) 중에 희석하였다. 각 웰에, 희석된 효소 12 μL를 시험 억제제 또는 대조군 비히클 디메틸술폭시드 (DMSO) 0.5 μL와 간단히 혼합하였다. ATP 및 His6-S6K를 함유한 키나제 검정 완충액 12.5 μL를 첨가하여 800 ng/ml FLAG-TOR, 100 mM ATP 및 1.25 mM His6-S6K를 함유한 최종 반응 부피 25 μL를 제공함으로써 키나제 반응을 개시하였다. 반응 플레이트를 완만하게 진탕시키면서 실온에서 2 시간 동안 (1 내지 6 시간에 선형) 인큐베이션한 후에, 스톱 완충액 (20 mM HEPES (pH 7.4), 20 mM EDTA, 20 mM EGTA) 25 μL를 첨가하여 종결시켰다. 인산화 (Thr-389) His6-S6K의 델피아 검출은 유로퓸-N1-ITC (Eu) (항체 당 10.4 Eu, 퍼킨엘머)로 표지된 모노클로날 항-p(T389)-p70S6K 항체 (1A5, 셀 시그날링)를 사용하여 실온에서 수행하였다. 델피아 검정 완충액 및 증강 용액은 퍼킨엘머로부터 구입할 수 있다. 종결된 키나제 반응 혼합물 45 μL를 PBS 55 μL를 함유하는 맥시소르프 플레이트 (넝크(Nunc))로 전달하였다. His6-S6K를 2 시간 동안 부착시키고, 그 후에 웰을 흡인시키고, PBS로 1회 세척하였다. 40 ng/ml Eu-P(T389)-S6K 항체를 함유한 델피아 검정 완충액 100 μL를 첨가하였다. 완만하게 교반하면서 항체 결합을 1 시간 동안 계속하였다. 이어서, 웰을 흡인시키고, 0.05％ 트윈-20을 함유하는 PBS (PBST)로 4회 세척하였다. 델피아 증강 용액 100 μL를 각 웰에 첨가하고, 플레이트를 퍼킨엘머 빅터 모델 플레이트 리더에서 판독하였다. 수득된 데이터는 효소적 활성, 및 잠재적 억제제에 의한 효소 억제를 계산하는데 사용하였다. Human mTOR assays using purified enzymes (see Toral-Barza, et al. Biochem Biophys. Res. Commun. 2005 June 24; 332 (1): 304-10) are described as DELFIA. It was performed in 96-well plates according to the format. First, the enzyme was added in kinase assay buffer (10 mM HEPES (pH 7.4), 50 mM NaCl, 50 mM β-glycerophosphate, 10 mM MnCl 2 , 0.5 mM DTT, 0.25 mM microcystine LR and 100 mg / ml BSA). Diluted. In each well, 12 μL of diluted enzyme was briefly mixed with 0.5 μL of test inhibitor or control vehicle dimethylsulfoxide (DMSO). Kinase reactions were initiated by adding 12.5 μL of kinase assay buffer containing ATP and His6-S6K to provide a final reaction volume of 25 μL containing 800 ng / ml FLAG-TOR, 100 mM ATP and 1.25 mM His6-S6K. The reaction plates were incubated for 2 hours (linear at 1-6 hours) at room temperature with gentle shaking, followed by the addition of 25 μL of stop buffer (20 mM HEPES (pH 7.4), 20 mM EDTA, 20 mM EGTA). . Delphia detection of phosphorylated (Thr-389) His6-S6K was performed with monoclonal anti-p (T389) -p70S6K antibody (1A5, cell labeled with Europium-N1-ITC (Eu) (10.4 Eu per antibody, PerkinElmer). Signaling) at room temperature. Delfia assay buffer and enhancement solution can be purchased from PerkinElmer. 45 μL of the terminated kinase reaction mixture was transferred to a Maxithorpe plate (Nunc) containing 55 μL of PBS. His6-S6K was attached for 2 hours, after which the wells were aspirated and washed once with PBS. 100 μL of Delphia assay buffer containing 40 ng / ml Eu-P (T389) -S6K antibody was added. Antibody binding was continued for 1 hour with gentle stirring. The wells were then aspirated and washed four times with PBS (PBST) containing 0.05% Tween-20. 100 μL of Delphia enhancement solution was added to each well and plates were read on a PerkinElmer Victor Model Plate Reader. The data obtained were used to calculate enzymatic activity and enzyme inhibition by potential inhibitors.

PI3K-알파 및 PI3K-감마 형광 편광 검정 프로토콜PI3K-alpha and PI3K-gamma Fluorescence Polarization Assay Protocols

반응 완충액은 20 mM HEPES, pH 7.5, 2 mM MgCl2, 0.05％ CHAPS 및 0.01％ βME (새로 첨가됨)였다. 스톱/검출 완충액은 100 mM HEPES, pH 7.5, 4 mM EDTA, 0.05％ CHAPS; 물 중 ATP 20 mM; 물 중 PIP2 (디C8, 에셀론, 솔트 레이크 시티 유타 카탈로그 # P-4508) 1 mM (MW=856.5)이었다. GST-GRP는 10％ 글리세롤 중 1.75 mg/ml 또는 1.4 mg/ml였다. 레드 검출기 (TAMRA)는 2.5 μM이었다. 넝크 384-웰 흑색 폴리프로필렌 형광 플레이트는 PI3K 검정에 사용하였다. The reaction buffer was 20 mM HEPES, pH 7.5, 2 mM MgCl 2 , 0.05% CHAPS and 0.01% βME (newly added). Stop / detect buffers are 100 mM HEPES, pH 7.5, 4 mM EDTA, 0.05% CHAPS; ATP 20 mM in water; PIP2 (DiC8, Ecelon, Salt Lake City Utah Catalog # P-4508) in water was 1 mM (MW = 856.5). GST-GRP was 1.75 mg / ml or 1.4 mg / ml in 10% glycerol. Red detector (TAMRA) was 2.5 μΜ. Shank 384-well black polypropylene fluorescent plates were used for the PI3K assay.

웰 당 희석된 효소 5 μL을 넣어 검정을 진행한 후에, 희석된 화합물 5 μL (또는 DMSO 중 효소 9.5 μL 및 이어서 화합물 0.5 μL)를 첨가하고 혼합하였다. 이어서, 기질 10 μL를 첨가하여 반응을 시작하였다. 샘플은 30 내지 60 분 인큐베이션한 후에, 20 μL 스톱/검출 혼합을 첨가함으로써 반응을 중단시켰다. PI3K를 반응 완충액으로 희석하고 (예를 들면, PI3K 5 μL 또는 7.5 μL를 반응 완충액 620 μL 내로), 웰 당 희석된 효소 5 μL를 사용하였다. 반응 완충액, 또는 완충액에 희석된 약물 5 μL 부분 (예를 들면, 4 μL/100, 최종 DMSO는 반응물 중 1％임)을 각각에 첨가하였다. 상하로 피펫팅하여 샘플을 혼합하였다. 별법으로, 효소를 1215 μL로 희석시킬 수 있다. 이 경우에 웰 당 9.8 μL를 첨가하고, 화합물 0.2 μL를 DMSO 중에 첨가하였다. After assaying with 5 μL of diluted enzyme per well, 5 μL of diluted compound (or 9.5 μL of enzyme in DMSO and then 0.5 μL of compound) were added and mixed. The reaction was then started by adding 10 μL of substrate. After the sample was incubated for 30 to 60 minutes, the reaction was stopped by adding 20 μL stop / detection mix. PI3K was diluted with reaction buffer (eg 5 μL or 7.5 μL of PI3K into 620 μL of reaction buffer) and 5 μL of enzyme diluted per well was used. A reaction buffer, or 5 μL portion of drug diluted in buffer (eg 4 μL / 100, final DMSO is 1% of reaction) was added to each. Samples were mixed by pipetting up and down. Alternatively, the enzyme can be diluted to 1215 μL. In this case 9.8 μL per well was added and 0.2 μL of compound was added in DMSO.

기질 용액 1 mL을 제조하기 위해, 반응 완충액 955 μL, PIP2 40 μL 및 ATP 2.5 μL를 혼합하였다. 기질 10 μL를 각 웰에 첨가하여 반응을 시작하였다. 이것은 반응 당 20 μM PIP2 및 25 μM ATP을 생성하였다. 스톱/검출기 혼합은 레드 검출기 4 μL 및 GST-GRP 1.6 μL 또는 2.0 μL를 스톱 완충액 1 mL와 함께 혼합함으로써 제조하여, 10 nM 프로브 및 70 nM GST-GRP를 생성하였다. 스톱/검출기 혼합 20 μL를 각 웰에 첨가하여 반응을 중단시켰다. 적색 프로브 용액을 암색으로 유지한 30 내지 90 분 후에 플레이트를 판독하였다. 0 시점을 위해, 기질을 첨가하기 직전에 스톱/검출기 혼합을 효소에 첨가하였다. 여분의 대조군을 위해, 스톱/검출기 혼합을 완충액 (효소 없음) 및 기질 또는 단지 완충액 (기질 없음)에 첨가하였다. 모은 PI3K 제제는 0.25 mg/mL의 단백질 농도를 가졌다. 추천된 반응물을 20 μL 당 0.06 μL (0.015 μg/20 μL) 또는 0.01125 μg/15 μL 또는 0.75 μg/mL을 가졌다. To prepare 1 mL of substrate solution, 955 μL of reaction buffer, 40 μL of PIP2 and 2.5 μL of ATP were mixed. The reaction was started by adding 10 μL of substrate to each well. This produced 20 μM PIP2 and 25 μM ATP per reaction. Stop / detector mixing was prepared by mixing 4 μL of red detector and 1.6 μL or 2.0 μL of GST-GRP with 1 mL of stop buffer, resulting in a 10 nM probe and 70 nM GST-GRP. The reaction was stopped by adding 20 μL of stop / detector mix to each well. The plate was read 30 to 90 minutes after the red probe solution remained dark. For time zero, a stop / detector mix was added to the enzyme just prior to adding the substrate. For extra control, stop / detector mix was added to the buffer (no enzyme) and the substrate or only buffer (no substrate). The pooled PI3K formulations had a protein concentration of 0.25 mg / mL. The recommended reaction had 0.06 μL (0.015 μg / 20 μL) or 0.01125 μg / 15 μL or 0.75 μg / mL per 20 μL.

플레이트를 TAMRA용 필터가 장착된 기계에서 판독하였다. 유닛은 mP로 나타내며, 효소 무함유 대조군은 app 190-220 mP로 판독되었다. 완전 활성 효소는 30 분 후에 70-100 mP 아래로 형광 편광을 감소시켰다. 활성 화합물은 mP 값을 대조군의 중간 또는 120-150 mP 유닛으로 상승시켰다. Plates were read on a machine equipped with a filter for TAMRA. Units are expressed in mP and enzyme-free control was read with app 190-220 mP. Fully active enzyme reduced fluorescence polarization below 70-100 mP after 30 minutes. The active compound raised the mP value to the middle of the control or to 120-150 mP units.

시험관내 세포 배양 성장 검정 방법In vitro cell culture growth assay method

사용된 세포주는 인간 유방 MDA-MB-361, 인간 전립선 PC3-mm2 및 인간 전립선 LNCap 종양 세포주이다. 세포를 웰 당 대략 3000개 세포로 96-웰 배양 플레이트에 플레이팅하였다. 플레이팅 다음날, DMSO 중 다양한 농도의 PI3K 억제제를 세포에 첨가하였다 (세포 검정 중 최종 DMSO 농도가 0.25％임). 약물 처리 3일 후에, 생세포 밀도를 염료 MTS (시험관내 세포 증식의 잘 확립되어 있는 지시인자)의 세포 매개의 대사성 전환에 의해 측정하였다. 세포 성장 검정은 벤더에 의해 제공된 프로토콜을 따라, 프로메가 코포레이션 (위스콘신주 매디슨 소재)으로부터 구입한 키트를 사용하여 수행하였다. 490 nm에서의 측정 흡광도는 MTS 검정 결과를 생성하였다. 세포 증식에 대한 화합물 효과는 처리되지 않은 대조군 세포 성장과 관련하여 평가하였다. 성장의 50％ 억제를 부여하는 약물 농도는 IC50 (μM)으로 측정되었다. The cell lines used are human breast MDA-MB-361, human prostate PC3-mm2 and human prostate LNCap tumor cell lines. Cells were plated in 96-well culture plates at approximately 3000 cells per well. The day after plating, various concentrations of PI3K inhibitor in DMSO were added to the cells (final DMSO concentration in the cell assay was 0.25%). Three days after drug treatment, viable cell density was measured by cell mediated metabolic conversion of dye MTS (a well established indicator of in vitro cell proliferation). Cell growth assays were performed using a kit purchased from Promega Corporation (Madison, Wisconsin), following the protocol provided by the vendor. The measured absorbance at 490 nm produced the results of the MTS assay. Compound effect on cell proliferation was assessed with respect to untreated control cell growth. Drug concentration conferring 50% inhibition of growth was determined as IC 50 (μM).

hSMG-1 키나제 검정hSMG-1 Kinase Test

인간 SMG-1 (hSMG-1) 키나제 검정은 일시적으로 감염된 HEK293 세포로부터 제조된 재조합 hSMG-1 단백질 및 세포 종양 저해인자 유전자 p53에서 파생된 GST-p53 (aa 1-70) 융합 기질 단백질을 사용하였다. 통상의 검정은 다음과 같이 96-웰 플레이트 포맷으로 실행하였다. 먼저, 효소를 키나제 검정 완충액 (10 mM HEPES, pH 7.4, 50 mM NaCl, 0.2 mM DTT, 50 mM β-글리세로포스페이트, 0.5 μM 마이크로시스틴 LR, 10 mM MnCl2) 중에 희석하였다. 각 웰에, 희석된 효소 12 μL를 시험 억제제 또는 대조군 비히클 디메틸술폭시드 (DMSO) 0.5 μL와 간단히 혼합하였다. ATP 및 GST-p53을 함유한 키나제 검정 완충액 12.5 μL를 첨가하여 400-800 ng/ml FLAG-hSMG-1, 0.5 μg GST-p53, 10 μM ATP를 함유한 최종 반응 부피 25 μL를 제공함으로써 키나제 반응을 개시하였다. 1.0 시간 동안 실온에서 반응을 수행한 후에, 스톱 용액 25 μl를 첨가함으로써 종결시켰다. 이어서, 검정 혼합물을 맥시소르프 표면을 가진 플루오로넝크 플레이트 (넝크 #439454)로 전달하였다. 플레이트를 2 시간 동안 실온에서 (밤새 4℃에서) 인큐베이션하여 플레이트에 대한 기질 단백질의 효율적인 결합을 달성하였다. 플레이트를 흡인시키고, PBS로 세척하였다. 델피아 검정 완충액 100 μl (퍼킨엘머 #1244-111) 중 125 ng의 유로퓸-표지된 항-생쥐 2차 항체 (퍼킨엘머 AD2027) 및 1차 포스포(S15)-p53 모노클로날 항체 (셀 시그날 #9286)와 함께 1 시간 동안 인큐베이션함으로써, 포스포-기질 단백질을 검출하였다. 이어서, 플레이트를 세척하고, 델피아 증강 용액 (퍼킨엘머 #1244-105) 100 μl와 함께 0.5 시간 동안 인큐베이션하였다. 델피아 검정 결과는 빅터 플레이트 리더 (퍼킨엘머)에서 기록하였다. 수득된 데이터는 효소적 활성, 및 잠재적 억제제에 의한 효소 억제를 계산하는데 사용하였다. The human SMG-1 (hSMG-1) kinase assay used a recombinant hSMG-1 protein prepared from transiently infected HEK293 cells and a GST-p53 (aa 1-70) fusion substrate protein derived from the cell tumor suppressor gene p53. . Conventional assays were performed in 96-well plate format as follows. First, the enzyme was diluted in kinase assay buffer (10 mM HEPES, pH 7.4, 50 mM NaCl, 0.2 mM DTT, 50 mM β-glycerophosphate, 0.5 μM microcystine LR, 10 mM MnCl 2 ). In each well, 12 μL of diluted enzyme was briefly mixed with 0.5 μL of test inhibitor or control vehicle dimethylsulfoxide (DMSO). Kinase reaction by adding 12.5 μL of kinase assay buffer containing ATP and GST-p53 to give a final reaction volume of 25 μL containing 400-800 ng / ml FLAG-hSMG-1, 0.5 μg GST-p53, 10 μM ATP Started. After the reaction was conducted at room temperature for 1.0 hour, it was terminated by adding 25 μl of stop solution. The assay mixture was then transferred to a fluoroshank plate (Maxk # 439454) with a Maxithorpe surface. Plates were incubated for 2 hours at room temperature (at 4 ° C. overnight) to achieve efficient binding of the substrate protein to the plates. The plate was aspirated and washed with PBS. 125 ng of europium-labeled anti-mouse secondary antibody (PerkinElmer AD2027) and primary phospho (S15) -p53 monoclonal antibody (cell signal) in 100 μl of Delpia assay buffer (PerkinElmer # 1244-111) Phospho-substrate protein was detected by incubation for 1 hour. Plates were then washed and incubated with 100 μl of Delphiia enhancement solution (PerkinElmer # 1244-105) for 0.5 hours. Delfia test results were recorded in Victor Plate Reader (Perkin Elmer). The data obtained were used to calculate enzymatic activity and enzyme inhibition by potential inhibitors.

표 2는 기술된 PI3K-α, PI3K-γ 및 mTOR 키나제 검정의 결과를 보여준다. Table 2 shows the results of the described PI3K-α, PI3K-γ and mTOR kinase assays.

Figure 112010076169004-pct00101
Figure 112010076169004-pct00101

Figure 112010076169004-pct00102
Figure 112010076169004-pct00102

Figure 112010076169004-pct00103
Figure 112010076169004-pct00103

Figure 112010076169004-pct00104
Figure 112010076169004-pct00104

Figure 112010076169004-pct00105
Figure 112010076169004-pct00105

Figure 112010076169004-pct00106
Figure 112010076169004-pct00106

Figure 112010076169004-pct00107
Figure 112010076169004-pct00107

Figure 112010076169004-pct00108
Figure 112010076169004-pct00108

Figure 112010076169004-pct00109
Figure 112010076169004-pct00109

Figure 112010076169004-pct00110
Figure 112010076169004-pct00110

Figure 112010076169004-pct00111
Figure 112010076169004-pct00111

Figure 112010076169004-pct00112
Figure 112010076169004-pct00112

Figure 112010076169004-pct00113
Figure 112010076169004-pct00113

Figure 112010076169004-pct00114
Figure 112010076169004-pct00114

Figure 112010076169004-pct00115
Figure 112010076169004-pct00115

Figure 112010076169004-pct00116
Figure 112010076169004-pct00116

Figure 112010076169004-pct00117
Figure 112010076169004-pct00117

Figure 112010076169004-pct00118
Figure 112010076169004-pct00118

Figure 112010076169004-pct00119
Figure 112010076169004-pct00119

Figure 112010076169004-pct00120
Figure 112010076169004-pct00120

Figure 112010076169004-pct00121
Figure 112010076169004-pct00121

표 3은 기술된 hSMG-1 키나제 검정의 결과를 보여준다. Table 3 shows the results of the described hSMG-1 kinase assay.

Figure 112010076169004-pct00122
Figure 112010076169004-pct00122

표 4는 기술된 MDA-MB-361, PC3-mm2 및 LNCap 검정의 결과를 보여준다. Table 4 shows the results of the MDA-MB-361, PC3-mm2 and LNCap assays described.

Figure 112010076169004-pct00123
Figure 112010076169004-pct00123

Figure 112010076169004-pct00124
Figure 112010076169004-pct00124

Figure 112010076169004-pct00125
Figure 112010076169004-pct00125

Figure 112010076169004-pct00126
Figure 112010076169004-pct00126

Figure 112010076169004-pct00127
Figure 112010076169004-pct00127

Figure 112010076169004-pct00128
Figure 112010076169004-pct00128

Figure 112010076169004-pct00129
Figure 112010076169004-pct00129

Figure 112010076169004-pct00130
Figure 112010076169004-pct00130

Figure 112010076169004-pct00131
Figure 112010076169004-pct00131

Figure 112010076169004-pct00132
Figure 112010076169004-pct00132

Figure 112010076169004-pct00133
Figure 112010076169004-pct00133

Figure 112010076169004-pct00134
Figure 112010076169004-pct00134

Figure 112010076169004-pct00135
Figure 112010076169004-pct00135

Figure 112010076169004-pct00136
Figure 112010076169004-pct00136

Figure 112010076169004-pct00137
Figure 112010076169004-pct00137

Figure 112010076169004-pct00138
Figure 112010076169004-pct00138

Figure 112010076169004-pct00139
Figure 112010076169004-pct00139

Figure 112010076169004-pct00140
Figure 112010076169004-pct00140

Figure 112010076169004-pct00141
Figure 112010076169004-pct00141

Figure 112010076169004-pct00142
Figure 112010076169004-pct00142

본 발명의 특정 측면이 설명되고 기술되지만, 다양한 다른 변화 및 변형이 본 발명의 취지 및 범주에서 벗어나지 않고 만들어질 수 있다는 것이 당업자들에게 명백할 것이다. 따라서, 그것은 하기 첨부된 특허청구범위에서 본 발명의 범주내에 있는 모든 그와 같은 변화 및 변형을 포함하도록 의도된다. While certain aspects of the invention have been described and described, it will be apparent to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. Accordingly, it is intended to embrace all such variations and modifications as fall within the scope of the invention in the appended claims.

본원 전체에 걸쳐 다양한 문헌이 인용된다. 그들의 전체의 이러한 문헌의 개시는 본원에 참조로서 포함되어, 본원에서 기술되고 청구된 본 발명의 현재에 그 숙련자들에게 공지된 바와 같이 당업계의 기술을 더 완전히 기재한다. Various documents are cited throughout this application. The entire disclosure of these documents is incorporated herein by reference to more fully describe the art of the art as known to those skilled in the art of the present invention described and claimed herein.

Claims (26)

하기 화학식 I의 화합물 또는 그의 제약상 허용되는 염:
<화학식 I>
Figure 112013054133712-pct00143

상기 식 중,
R1은
Figure 112013054133712-pct00161
이고;
R2는 임의로 치환된 C6-C14아릴-NH-COR3이고;
R3은 OR5, NR5R5 또는 NHR5이고;
R5는 독립적으로 C1-C6알킬, C3-C6알케닐, C3-C6알키닐, 임의로 치환된 C6-C10아릴, C1-C6할로알킬, 임의로 치환된 C1-C9헤테로아릴, C1-C6히드록시알킬-, 및 OH, NR11R11 또는 3원 내지 7원 C1-C6헤테로시클릴로 임의로 치환된 C3-C10 포화 또는 불포화 모노 또는 비시클릭 C3-C10시클로알킬, 및 3원 내지 10원 포화 또는 불포화 모노 또는 비시클릭 C1-C9헤테로시클릴로 이루어진 군으로부터 선택되되, 단, 3원 시클로알킬 및 헤테로시클릴 고리는 포화된 것이거나;
또는 2개의 R5 기는, 이들이 부착되어 있는 질소 원자와 함께, C1-C6알킬로 임의로 치환된 3원 내지 8원 고리계를 형성하고, 여기서 상기 고리계는 포화 또는 불포화된 것이고, 상기 질소 원자 이외에, O, S, S(O), S(O)2 및 NR10으로부터 선택된 0 내지 2개의 헤테로원자 고리원을 갖고;
R10은 H, C1-C6알킬, -SO2(C1-C6알킬), -COO(C1-C6알킬), -CONH(C1-C6알킬), -CON(C1-C6알킬)2, -CO(C1-C6알킬) 및 -SO2NHR11로 이루어진 군으로부터 선택되고;
R11은 H, 및 OH 또는 3원 내지 7원 C1-C6헤테로시클릴로 임의로 치환된 C1-C6알킬, -CO(C1-C6알킬), 임의로 치환된 C6-C10아릴, 및 임의로 치환된 C1-C9헤테로아릴로 이루어진 군으로부터 선택되고;
R4는 a) i) C1-C6알킬-로 임의로 치환된 3원 내지 10원 C1-C9헤테로시클릴, ii) H2N-, iii) (C1-C6알킬)NH-, iv) (C1-C6알킬)2N-, v) NH(CH2)aN(C1-C6알킬)2 (여기서, a는 2, 3 또는 4임) 및 vi) CHO로 임의로 치환된 C1-C6알킬; b) C3-C6알케닐; c) C3-C6알키닐; d) -O-C1-C8알킬로 임의로 치환된 -O-C1-C8알킬; e) -O-C3-C8알케닐; f) -O-C3-C8알키닐; g) 포화 또는 불포화 모노 또는 비시클릭 C3-C8시클로알킬; 및 h) 포화 또는 불포화 모노 또는 비시클릭 -O-C3-C12시클로알킬 (이들 모두는 OH, NR11R11, 또는 C1-C6알킬-로 임의로 치환된 3원 내지 7원 C1-C6헤테로시클릴로 임의로 치환되고, 단, OH 또는 NR11R11은 또다른 탄소 원자에 대해 이중-결합 또는 삼중-결합된 탄소 원자에 직접 결합되지는 않음); i) -CH=CH-C6-C10아릴; j) -CH=CH-C1-C9헤테로아릴; k) 임의로 치환된 C6-C10아릴; l) 탄소 원자를 통해 트리아진 잔기에 부착된, 임의로 치환된 5원 내지 10원 C1-C9헤테로아릴; m) 탄소 또는 질소 원자를 통해 트리아진 잔기에 부착되고, OH, NR11R11, C1-C6알킬, (C1-C6알킬)아미도-, (C1-C6알킬)C(O)-, (C1-C6알콕시)카르보닐-, 아다만틸, C1-C6히드록실알킬-, (C1-C6알킬)아미도- 또는 3원 내지 7원 C1-C6헤테로시클릴로부터 독립적으로 선택되는 1 내지 3개의 치환기로 임의로 치환된 3원 내지 10원 포화 또는 불포화 모노시클릭 C1-C9헤테로시클릴 (단, 3원 헤테로시클릴은 포화된 것이고, 질소 원자를 통해 트리아진 잔기에 부착되며, 5원 비시클릭 헤테로시클릴은 포화된 것임); n) 임의로 치환된 -O-C6-C10아릴; o) 임의로 치환된 -O-C1-C9헤테로아릴; p) (C1-C6알콕시)카르보닐-, H2NS(O)2-, 또는 OH, NR11R11 또는 3원 내지 7원 C1-C6헤테로시클릴로 임의로 더 치환된 C1-C6알킬로 임의로 치환된 -O-(3원 내지 12원 포화 또는 불포화 모노 또는 비시클릭)C1-C9헤테로시클릴 (단, 3원 헤테로시클릴은 포화된 것임); q) -NHC6-C10아릴; r) -NHC1-C9헤테로아릴; s) -NHNH2; t) -NHNHC1-C6알킬; u) -NHN(C1-C6알킬)2; v) -NHOH; w) -COOH; x) -COO-C1-C6알킬; y) -CONR12R13; z) -NR12R13;
Figure 112013054133712-pct00146

(여기서, Z는 CH2, O, S(O)n 또는 NR10이고, n은 0, 1 또는 2임); ee) 할로겐; ff) C6-C14아릴-S(O)2-NH-; gg) R11NHC(O)NH-O- 및 hh) 질소 원자를 통해 트리아진 잔기에 부착된, 임의로 치환된 5원 모노시클릭 C1-C4헤테로아릴로 이루어진 군으로부터 선택되고;
R12 및 R13은 각각 독립적으로 H, 임의로 일치환 또는 이치환된 C1-C8알킬, 임의로 치환된 C3-C8알케닐, 및 임의로 치환된 C3-C8알키닐로부터 선택되거나 (임의의 치환기는 C1-C6알콕시, OH, NR11R11 및 3원 내지 7원 C1-C6헤테로시클릴로부터 선택되되, 단, OH 또는 NR11R11은 또다른 탄소 원자에 이중-결합 또는 삼중-결합된 탄소 원자에 직접 결합되지는 않음);
또는 R12 및 R13은, 이들이 부착되어 있는 질소 원자와 함께, C1-C6알킬로 임의로 치환된 3원 내지 8원 모노시클릭 고리계를 형성하거나 (여기서, 상기 고리계는 포화 또는 불포화된 것이고, 상기 질소 원자 이외에, O, S(O)n 및 NR10으로부터 선택된 0 내지 2개의 헤테로원자 고리원을 가짐);
또는 R12 및 R13은, 이들이 부착되어 있는 질소 원자와 함께,
Figure 112013054133712-pct00147

(여기서, a 및 b는 각각 독립적으로 -CH2-, O, S 또는 NR10이고, x는 1 내지 3임)를 형성하고;
C1-C9헤테로아릴은 하나 이상의 고리, 및 O, NR10 및 S(O)n으로부터 독립적으로 선택된 1, 2, 3 또는 4개의 고리원을 갖는 5원 내지 10원 방향족 고리계를 지칭하고;
C1-C9헤테로시클릴은 하나 이상의 고리, 및 O, NR10 및 S(O)n으로부터 독립적으로 선택된 1, 2, 3 또는 4개의 고리원을 갖는 3원 내지 10원 고리계를 지칭하고;
임의로 치환된 아릴기 및 헤테로아릴기는 비치환되거나, 또는 a) OH, NH2, NH(C1-C6알킬), N(C1-C6알킬)2, -NH(CH2)wN(C1-C6알킬)2 (여기서, w는 2, 3 또는 4임), 또는 C1-C6알킬- 치환기로부터 독립적으로 선택된 1 내지 3개로 임의로 치환된 3원 내지 10원 C1-C9헤테로시클릴로 임의로 치환된 C1-C6알킬; b) 할로겐; c) 히드록시; d) NH2; e) NO2; f) SO2NH2; g) COOH; h) COO(C1-C6알킬); i) NHCOO(C1-C6알킬); j) NH(C1-C6알킬); k) N(C1-C6알킬)2; l) C(O)NRaRb (여기서, Ra는 H 또는 C1-C6알킬이고, Rb는 H, C1-C6알킬, (C6-C14아릴)알킬- 또는 (C1-C9헤테로아릴)알킬-임); m) -Y-Q (여기서, Y는 i) O, ii) NH, iii) N(C1-C6알킬), iv) NHSO2, v) SO2NH, vi) NHCONH, vii) NHCON(C1-C6알킬), viii) S(O)q (q는 0, 1 또는 2임), ix) -C(O)NH-, x) -NHC(O)-, xi) -C(O)N(CH3)-, xii) C(O)이거나 또는 xiii) 존재하지 않고, Q는 i) A) 1) H2N-, 2) (C1-C6알킬)아미노-, 3) 디(C1-C6알킬)아미노-, 4) C1-C6알킬-에 의해 임의로 치환된 C1-C9헤테로시클릴-, 또는 5) 히드록실로 임의로 치환된 C1-C6알콕시-, B) (C1-C6알콕시)카르보닐-, C) (C1-C6알콕시)C(O)NH-, D) 1) H2N-, 2) (C1-C6알킬)아미노- 또는 3) 디(C1-C6알킬)아미노-로 임의로 치환된 C1-C6알킬-, E) (C1-C6알킬)아미노-, F) 디(C1-C6알킬)아미노-, G) 1) H2N-, 2) (C1-C6알킬)아미노- 또는 3) 디(C1-C6알킬)아미노-로 임의로 치환된 (C1-C6알킬)아미도-, H) (C1-C6알킬)카르복시아미도-, I) C1-C6알킬- 또는 C1-C6히드록실알킬-로 임의로 치환된 C1-C9헤테로시클릴-, J) C1-C6알킬-로 임의로 치환된 헤테로시클릴(C1-C6알킬)-, K) 할로겐, L) 히드록실, M) C1-C6히드록실알킬-, N) 퍼플루오로(C1-C6)알킬-, O) H2N-, P) O2N-, Q) H2NSO2-, R) HO2C- 및 S) NC-로부터 독립적으로 선택된 1 내지 3개의 치환기로 임의로 치환된 C6-C10아릴, ii) A) 1) H2N-, 2) (C1-C6알킬)아미노-, 3) 디(C1-C6알킬)아미노-, 4) C1-C6알킬-로 임의로 치환된 C1-C9헤테로시클릴- 또는 5) 히드록실로 임의로 치환된 C1-C6알콕시-, B) (C1-C6알콕시)카르보닐-, C) (C1-C6알콕시)C(O)NH-, D) 1) H2N-, 2) (C1-C6알킬)아미노- 또는 3) 디(C1-C6알킬)아미노-로 임의로 치환된 C1-C6알킬-, E) (C1-C6알킬)아미노-, F) 디(C1-C6알킬)아미노-, G) 1) H2N-, 2) (C1-C6알킬)아미노- 또는 3) 디(C1-C6알킬)아미노-로 임의로 치환된 (C1-C6알킬)아미도-, H) (C1-C6알킬)카르복시아미도-, I) C1-C6알킬- 또는 C1-C6히드록실알킬-로 임의로 치환된 C1-C9헤테로시클릴-, J) C1-C6알킬-로 임의로 치환된 헤테로시클릴(C1-C6알킬)-, K) 할로겐, L) 히드록실, M) C1-C6히드록실알킬-, N) 퍼플루오로(C1-C6)알킬-, O) H2N-, P) O2N-, Q) H2NSO2-, R) HO2C- 및 S) NC-로부터 독립적으로 선택된 1 내지 3개의 치환기로 임의로 치환된 5원 내지 10원 C1-C9헤테로아릴, iii) A) C1-C6알킬-, B) 헤테로시클릴(C1-C6알킬)-, C) (C6-C14아릴)알킬-, D) C1-C8아실-, E) (C1-C6알콕시)카르보닐-, F) (C1-C6알킬)카르복실-, G) 할로겐, H) C1-C6할로알킬-, I) 히드록실, J) C1-C6히드록시알킬-, K) H2N-, L) (C1-C6알킬)아미노-, M) 디(C1-C6알킬)아미노-, N) HO2C-, O) (C1-C6알콕시)카르보닐-, P) (C1-C6알킬)카르복실-, Q) (C1-C6알킬)아미도-, R) H2NC(O)-, S) (C1-C6알킬)카르복시아미도-, T) 5원 내지 10원 C1-C9헤테로아릴, U) C6-C14아릴, V) C3-C8시클로알킬, W) 3원 내지 10원 C1-C9헤테로시클릴, X) NC- 및 Y) -NO2로부터 독립적으로 선택된 1 내지 3개의 치환기로 임의로 치환된 3원 내지 10원 C1-C9헤테로시클릴, iv) C3-C10시클로알킬, v) C1-C6알킬, vi) C2-C6알케닐, vii) C2-C6알키닐, viii) C1-C6히드록시알킬-, ix) (CH2)vO(C1-C6알킬), x) (CH2)vNH2, xi) (CH2)vNH(C1-C6알킬), xii) (CH2)vN(C1-C6알킬)2, xiii) O(CH2)vN(C1-C6알킬)2, xiv) (CH2)vC6-C10아릴, xv) -CN, xvi) (CH2)v 5원 내지 10원 C1-C9헤테로아릴, xvii) C1-C6알킬-로 임의로 치환된 (CH2)v 3원 내지 10원 C1-C9헤테로시클릴 (여기서, v는 1, 2, 3 또는 4임) 및 xviii) C1-C6퍼플루오로알킬-로부터 선택됨); 및 n) C(O)Rc (여기서, Rc는 i) H, ii) C1-C6알킬 또는 iii) C3-C6시클로알킬임)로 이루어진 군으로부터 선택된 1 또는 2개의 잔기로 치환된다.A compound of formula (I) or a pharmaceutically acceptable salt thereof:
(I)
Figure 112013054133712-pct00143

Wherein,
R 1 is
Figure 112013054133712-pct00161
ego;
R 2 is optionally substituted C 6 -C 14 aryl-NH-COR 3 ;
R 3 is OR 5 , NR 5 R 5 or NHR 5 ;
R 5 is independently C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, optionally substituted C 6 -C 10 aryl, C 1 -C 6 haloalkyl, optionally substituted C C 3 -C 10 saturated or unsaturated mono optionally substituted with 1- C 9 heteroaryl, C 1 -C 6 hydroxyalkyl-, and OH, NR 11 R 11 or 3- to 7-membered C 1 -C 6 heterocyclyl Or bicyclic C 3 -C 10 cycloalkyl, and 3 to 10 membered saturated or unsaturated mono or bicyclic C 1 -C 9 heterocyclyl, provided that the 3 membered cycloalkyl and heterocyclyl ring is Saturated;
Or two R 5 groups together with the nitrogen atom to which they are attached form a three to eight membered ring system optionally substituted with C 1 -C 6 alkyl, wherein the ring system is saturated or unsaturated, and the nitrogen In addition to an atom, it has 0 to 2 heteroatomic ring members selected from O, S, S (O), S (O) 2 and NR 10 ;
R 10 is H, C 1 -C 6 alkyl, -SO 2 (C 1 -C 6 alkyl), -COO (C 1 -C 6 alkyl), -CONH (C 1 -C 6 alkyl), -CON (C 1 -C 6 alkyl) 2 , -CO (C 1 -C 6 alkyl) and -SO 2 NHR 11 ;
R 11 is H, and C 1 -C 6 alkyl optionally substituted with OH or 3-7 membered C 1 -C 6 heterocyclyl, —CO (C 1 -C 6 alkyl), optionally substituted C 6 -C 10 Aryl, and optionally substituted C 1 -C 9 heteroaryl;
R 4 is a) i) 3- to 10-membered C 1 -C 9 heterocyclyl optionally substituted with C 1 -C 6 alkyl-, ii) H 2 N-, iii) (C 1 -C 6 alkyl) NH -, iv) (C 1 -C 6 alkyl) 2 N-, v) NH (CH 2 ) a N (C 1 -C 6 alkyl) 2 , wherein a is 2, 3 or 4 and vi) CHO C 1 -C 6 alkyl optionally substituted with; b) C 3 -C 6 alkenyl; c) C 3 -C 6 alkynyl; d) -OC 1 -C 8 alkyl optionally substituted with -OC 1 -C 8 alkyl; e) -OC 3 -C 8 alkenyl; f) -OC 3 -C 8 alkynyl; g) saturated or unsaturated mono or bicyclic C 3 -C 8 cycloalkyl; And h) 3- to 7-membered C 1 -C optionally substituted with saturated or unsaturated mono or bicyclic -OC 3 -C 12 cycloalkyl, all of which are optionally substituted with OH, NR 11 R 11 , or C 1 -C 6 alkyl- Optionally substituted with 6 heterocyclyl, provided that OH or NR 11 R 11 is not directly bonded to a double- or triple-bonded carbon atom for another carbon atom; i) -CH = CH-C 6 -C 10 aryl; j) -CH = CH-C 1 -C 9 heteroaryl; k) optionally substituted C 6 -C 10 aryl; l) an optionally substituted 5-10 membered C 1 -C 9 heteroaryl attached to the triazine residue via a carbon atom; m) attached to a triazine moiety via a carbon or nitrogen atom, OH, NR 11 R 11 , C 1 -C 6 alkyl, (C 1 -C 6 alkyl) amido-, (C 1 -C 6 alkyl) C (O)-, (C 1 -C 6 alkoxy) carbonyl-, adamantyl, C 1 -C 6 hydroxylalkyl-, (C 1 -C 6 alkyl) amido- or 3- to 7-membered C 1 3- to 10-membered saturated or unsaturated monocyclic C 1 -C 9 heterocyclyl optionally substituted with 1 to 3 substituents independently selected from -C 6 heterocyclyl, provided that the 3-membered heterocyclyl is saturated Attached to the triazine moiety via a nitrogen atom and the 5-membered bicyclic heterocyclyl is saturated); n) optionally substituted -OC 6 -C 10 aryl; o) optionally substituted -OC 1 -C 9 heteroaryl; p) (C 1 -C 6 alkoxy) carbonyl -, H 2 NS (O) 2 -, or OH, NR 11 R 11 or a 3-to 7-membered C 1 -C 6 heterocycle optionally further substituted by C 1 Lilo -O- (3- to 12-membered saturated or unsaturated mono or bicyclic) C 1 -C 9 heterocyclyl optionally substituted with -C 6 alkyl, provided that the 3-membered heterocyclyl is saturated; q) -NHC 6 -C 10 aryl; r) -NHC 1 -C 9 heteroaryl; s) -NHNH 2 ; t) -NHNHC 1 -C 6 alkyl; u) -NHN (C 1 -C 6 alkyl) 2 ; v) -NHOH; w) -COOH; x) -COO-C 1 -C 6 alkyl; y) -CONR 12 R 13 ; z) -NR 12 R 13 ;
Figure 112013054133712-pct00146

Wherein Z is CH 2 , O, S (O) n or NR 10 and n is 0, 1 or 2; ee) halogen; ff) C 6 -C 14 aryl-S (O) 2 -NH-; gg) R 11 NHC (O) NH-O- and hh) an optionally substituted 5-membered monocyclic C 1 -C 4 heteroaryl attached to a triazine residue via a nitrogen atom;
R 12 and R 13 are each independently selected from H, optionally mono- or di-substituted C 1 -C 8 alkyl, optionally substituted C 3 -C 8 alkenyl, and optionally substituted C 3 -C 8 alkynyl ( Optional substituents are selected from C 1 -C 6 alkoxy, OH, NR 11 R 11 and 3- to 7-membered C 1 -C 6 heterocyclyl, provided that OH or NR 11 R 11 is substituted at another carbon atom Not directly bonded to a bonded or triple-bonded carbon atom);
Or R 12 and R 13 together with the nitrogen atom to which they are attached form a 3- to 8-membered monocyclic ring system optionally substituted with C 1 -C 6 alkyl, wherein the ring system is saturated or unsaturated Having 0 to 2 heteroatom ring members selected from O, S (O) n and NR 10 in addition to the nitrogen atom;
Or R 12 and R 13 together with the nitrogen atom to which they are attached,
Figure 112013054133712-pct00147

Wherein a and b are each independently —CH 2 —, O, S or NR 10 and x is 1 to 3;
C 1 -C 9 heteroaryl refers to a 5-10 membered aromatic ring system having at least one ring and 1, 2, 3 or 4 ring members independently selected from O, NR 10 and S (O) n and ;
C 1 -C 9 heterocyclyl refers to a 3-10 membered ring system having at least one ring and 1, 2, 3 or 4 ring members independently selected from O, NR 10 and S (O) n and ;
Optionally substituted aryl and heteroaryl groups are unsubstituted or a) OH, NH 2 , NH (C 1 -C 6 alkyl), N (C 1 -C 6 alkyl) 2 , -NH (CH 2 ) w N (C 1 -C 6 alkyl) 2 , wherein w is 2, 3 or 4, or a 3 to 10 membered C 1 -optionally substituted with 1 to 3 independently selected from C 1 -C 6 alkyl- substituents. C 1 -C 6 alkyl optionally substituted with C 9 heterocyclyl; b) halogen; c) hydroxy; d) NH 2 ; e) NO 2 ; f) SO 2 NH 2 ; g) COOH; h) COO (C 1 -C 6 alkyl); i) NHCOO (C 1 -C 6 alkyl); j) NH (C 1 -C 6 alkyl); k) N (C 1 -C 6 alkyl) 2 ; l) C (O) NR a R b where R a is H or C 1 -C 6 alkyl, R b is H, C 1 -C 6 alkyl, (C 6 -C 14 aryl) alkyl- or ( C 1 -C 9 heteroaryl) alkyl-; m) -YQ, where Y is i) O, ii) NH, iii) N (C 1 -C 6 alkyl), iv) NHSO 2 , v) SO 2 NH, vi) NHCONH, vii) NHCON (C 1 -C 6 alkyl), viii) S (O) q (q is 0, 1 or 2), ix) -C (O) NH-, x) -NHC (O)-, xi) -C (O) N (CH 3 )-, xii) C (O) or xiii) absent, Q is i) A) 1) H 2 N-, 2) (C 1 -C 6 alkyl) amino-, 3) di (C 1 -C 6 alkyl) amino-a by optionally substituted C 1 -C 9 heterocyclyl, - -, 4) C 1 -C 6 alkyl, or 5) hydroxyl indeed, an optionally substituted C 1 -C 6 alkoxy -, B) (C 1 -C 6 alkoxy) carbonyl-, C) (C 1 -C 6 alkoxy) C (O) NH-, D) 1) H 2 N-, 2) (C 1 -C 6 Alkyl) amino- or 3) C 1 -C 6 alkyl-, E) (C 1 -C 6 alkyl) amino-, F) di (C 1 -optionally substituted with di (C 1 -C 6 alkyl) amino- C 6 alkyl) amino-, G) 1) H 2 N-, 2) (C 1 -C 6 alkyl) amino-, or 3) di (C 1 -C 6 alkyl) amino-optionally substituted with (C 1 - C 6 alkyl) amido-, H) (C 1 -C 6 alkyl) carboxamido-, I) C 1 -C 6 alkyl- or C 1 -C 6 hydroxylal Skill-in an optionally substituted C 1 -C 9 heterocyclyl, -, J) C 1 -C 6 alkyl-heterocyclyl, (C 1 -C 6 alkyl) optionally substituted with -, K) halogen, L) hydroxyl , M) C 1 -C 6 hydroxylalkyl-, N) perfluoro (C 1 -C 6 ) alkyl-, O) H 2 N-, P) O 2 N-, Q) H 2 NSO 2- , R) C 6 -C 10 aryl optionally substituted with 1 to 3 substituents independently selected from HO 2 C- and S) NC-, ii) A) 1) H 2 N-, 2) (C 1 -C 6 alkyl) amino-, 3) di (C 1 -C 6 alkyl) amino-a with an optionally substituted C 1 -C 9 heterocyclyl, - -, 4) C 1 -C 6 alkyl, or 5) hydroxyl chamber optionally substituted C 1 -C 6 alkoxy-, B) (C 1 -C 6 alkoxy) carbonyl-, C) (C 1 -C 6 alkoxy) C (O) NH-, D) 1) H 2 N-, 2) (C 1 -C 6 alkyl) amino- or 3) C 1 -C 6 alkyl-, E) (C 1 -C 6 alkyl) amino-, F optionally substituted with di (C 1 -C 6 alkyl) amino- ) Di (C 1 -C 6 alkyl) amino-, G) 1) H 2 N-, 2) (C 1 -C 6 alkyl) amino- or 3) di (C 1 -C 6 alkyl) amino- Substituted (C 1 -C 6 alkyl) amido-, H) (C 1 -C 6 alkyl) carboxamido-, I) optionally substituted with C 1 -C 6 alkyl- or C 1 -C 6 hydroxylalkyl- C 1 -C 9 heterocyclyl-optionally substituted heterocyclyl by (C 1 -C 6 alkyl) - -, J) C 1 -C 6 alkyl, K) halogen, L) hydroxyl, M) C 1 - C 6 hydroxylalkyl-, N) perfluoro (C 1 -C 6 ) alkyl-, O) H 2 N-, P) O 2 N-, Q) H 2 NSO 2- , R) HO 2 C- And S) 5- to 10-membered C 1 -C 9 heteroaryl optionally substituted with 1 to 3 substituents independently selected from NC-, iii) A) C 1 -C 6 alkyl-, B) heterocyclyl (C 1 -C 6 alkyl)-, C) (C 6 -C 14 aryl) alkyl-, D) C 1 -C 8 acyl-, E) (C 1 -C 6 alkoxy) carbonyl-, F) (C 1 -C 6 alkyl) carboxyl-, G) halogen, H) C 1 -C 6 haloalkyl-, I) hydroxyl, J) C 1 -C 6 hydroxyalkyl-, K) H 2 N-, L) (C 1 -C 6 alkyl) amino-, M) di (C 1 -C 6 alkyl) amino-, N) HO 2 C-, O) (C 1 -C 6 alkoxy) carbonyl-, P) (C 1- C 6 alkyl) carboxyl-, Q) (C 1 -C 6 alkyl) amido-, R) H 2 NC (O)-, S) (C 1 -C 6 alkyl) carboxamido-, T) 5-10 membered C 1 -C 9 heteroaryl, U) C 6 -C 14 aryl, V) C 3 -C 8 cycloalkyl, W) 3- to 10-membered C 1 -C 9 heterocyclyl, X) from NC- and Y) -NO 2 3- to 10-membered C 1 -C 9 heterocyclyl optionally substituted with independently selected 1 to 3 substituents, iv) C 3 -C 10 cycloalkyl, v) C 1 -C 6 alkyl, vi) C 2- C 6 alkenyl, vii) C 2 -C 6 alkynyl, viii) C 1 -C 6 hydroxyalkyl-, ix) (CH 2 ) v O (C 1 -C 6 alkyl), x) (CH 2 ) v NH 2 , xi) (CH 2 ) v NH (C 1 -C 6 alkyl), xii) (CH 2 ) v N (C 1 -C 6 alkyl) 2 , xiii) O (CH 2 ) v N (C 1 -C 6 alkyl) 2 , xiv) (CH 2 ) v C 6 -C 10 aryl, xv) -CN, xvi) (CH 2 ) v 5-10 membered C 1 -C 9 heteroaryl, xvii) C (CH 2 ) v 3- to 10-membered C 1 -C 9 heterocyclyl optionally substituted with 1- C 6 alkyl-, where v is 1, 2, 3 or 4 and xviii) C 1 -C 6 Perfluoroalkyl-); And n) C (O) R c , wherein R c is i) H, ii) C 1 -C 6 alkyl or iii) C 3 -C 6 cycloalkyl Is substituted. 삭제delete 삭제delete 제1항에 있어서, R2가 임의로 치환된 페닐-NH-COR3인 화합물.The compound of claim 1, wherein R 2 is optionally substituted phenyl-NH-COR 3 . 제4항에 있어서, R3이 NHR5인 화합물.The compound of claim 4, wherein R 3 is NHR 5 . 제5항에 있어서, R5가 임의로 치환된 페닐 또는 C1-C9헤테로아릴인 화합물.6. The compound of claim 5, wherein R 5 is optionally substituted phenyl or C 1 -C 9 heteroaryl. 제6항에 있어서, R5가 -Y-Q로 치환된 페닐인 화합물.The compound of claim 6, wherein R 5 is phenyl substituted with —YQ. 제7항에 있어서, -Y-가 C(O)인 화합물.8. A compound according to claim 7, wherein -Y- is C (O). 제8항에 있어서, Q가 디(C1-C6알킬)아미노-로 치환된 3원 내지 10원 C1-C9헤테로시클릴인 화합물.The compound of claim 8, wherein Q is a 3-10 membered C 1 -C 9 heterocyclyl substituted with di (C 1 -C 6 alkyl) amino-. 제1항에 있어서, R4가
Figure 112010076170983-pct00149
인 화합물 또는 그의 제약상 허용되는 염.The compound of claim 1, wherein R 4 is
Figure 112010076170983-pct00149
Or a pharmaceutically acceptable salt thereof. 제10항에 있어서, R4가
Figure 112010076170983-pct00150
인 화합물 또는 그의 제약상 허용되는 염.The compound of claim 10, wherein R 4 is
Figure 112010076170983-pct00150
Or a pharmaceutically acceptable salt thereof. 1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-3-일우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-페닐우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-티오펜-2-일우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-메틸페닐)우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-플루오로페닐)우레아;
1-(2,4-디메톡시페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-우레아;
1-(4-클로로페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-메톡시페닐)우레아;
(4-클로로페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
(2,4-디플루오로페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-에틸우레아;
tert-부틸 3-{[4-(4-{[(4-플루오로페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트;
tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(페닐카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트;
tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-3-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트;
tert-부틸 3-{[4-(4-{[(4-메틸페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]아미노}아제티딘-1-카르복실레이트;
1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-페닐우레아;
1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;
1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-플루오로페닐)우레아;
1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-메틸페닐)우레아;
tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)아미노]아제티딘-1-카르복실레이트;
1-{4-[4-(아제티딘-3-일아미노)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-[2-(디메틸아미노)에틸]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(2-메틸피리딘-4-일)우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(2-히드록시에틸)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-히드록시페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(1-히드록시에틸)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(트리플루오로메틸)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-히드록시페닐)우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[5-(트리플루오로메틸)피리딘-2-일]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[2,2,2-트리플루오로-1-히드록시-1-(트리플루오로메틸)에틸]페닐}우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[3-(1-히드록시에틸)페닐]우레아;
메틸 4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-페닐우레아;
1-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;
1-[4-(히드록시메틸)페닐]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;
1-(2-메틸피리딘-4-일)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;
1-[2-(메틸아미노)에틸]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;
1-(3-아세틸페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;
1-[4-(디메틸아미노)페닐]-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;
4-[3-{4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐}우레이도]벤조산;
N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드 HCl 염;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드;
N-(2-(디메틸아미노)에틸)-4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-모르폴리노피페리딘-1-카르보닐)페닐)우레아;
4-(3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(퀴누클리딘-3-일)벤즈아미드;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(피롤리딘-1-일)피페리딘-1-카르보닐)페닐)우레아;
1-(4-(1,4'-비피페리딘-1'-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(피리딘-2-일)아세틸)페닐)우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(1-히드록시에틸)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(2-메틸피리딘-4-일)우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(트리플루오로메틸)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[2,2,2-트리플루오로-1-히드록시-1-(트리플루오로메틸)에틸]페닐}우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[5-(트리플루오로메틸)피리딘-2-일]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[3-(1-히드록시에틸)페닐]우레아;
1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
1-[4-(2-히드록시에틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;
1-[4-(2-히드록시메틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;
1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(2-메틸피리딘-4-일)우레아;
1-[4-(1-히드록시에틸)페닐]-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;
1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
메틸 4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}-아미노)벤조에이트;
1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(1-메틸피페리딘-4-일)우레아;
1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(1-메틸피페리딘-4-일)우레아;
1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아;
1-{4-[4-모르폴린-4-일-6-(테트라히드로-피란-4-일)-[1,3,5]트리아진-2-일]-페닐}-3-피리딘-4-일-우레아;
3-({4-모르폴린-4-일-6-[4-(3-피리딘-4-일-우레이도)-페닐]-[1,3,5]트리아진-2-일아미노}-메틸)-아제티딘-1-카르복실산 tert-부틸 에스테르;
1-(4-{4-[(아제티딘-3-일메틸)-아미노]-6-모르폴린-4-일-[1,3,5]트리아진-2-일}-페닐)-3-피리딘-4-일-우레아;
1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;
1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-페닐우레아;
1-[4-(디메틸아미노)페닐]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-시아노페닐)-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(2-메틸피리딘-4-일)우레아;
1-[2-(디메틸아미노)에틸]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-[4-(4-모르폴린-4-일-6-퀴놀린-3-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
1-[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
메틸 4-({[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
1-[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;
4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피페리딘-1-일에틸)벤즈아미드;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(모르폴린-4-일카르보닐)페닐]우레아;
1-[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
4-({[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
4-({[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;
N-[2-(디메틸아미노)에틸]-N-메틸-4-({[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
1-[4-(4-메틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-(4-{[3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-({4-[2-(디메틸아미노)에틸]피페라진-1-일}카르보닐)페닐]-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-피롤리딘-1-일피페리딘-1-일)카르보닐]페닐}우레아;
4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;
1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-이소프로폭시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
4-({[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산; mp 204℃;
1-[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아; mp 170℃;
4-({[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;
4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;
1-{4-[4-(1-에톡시비닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-[4-(4-아세틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
메틸 4-[({4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;
1-{4-[4-(1-히드록시에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
메틸 4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;
4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;
1-(4-{4-모르폴린-4-일-6-[2-(피리딘-4-일아미노)에틸]-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[2-(디메틸아미노)에틸]벤즈아미드;
1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(히드록시메틸)페닐]우레아;
4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;
1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸-N-[2-(메틸아미노)에틸]벤즈아미드;
1-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-{4-[(3,3-디메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피페리딘-1-일에틸)벤즈아미드;
4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[4-(4-메틸피페라진-1-일)페닐]벤즈아미드;
1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-({[2-(디메틸아미노)에틸]아미노}메틸)페닐]우레아;
4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-[4-(4-메틸피페라진-1-일)페닐]벤즈아미드;
1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)메틸]페닐}우레아;
1-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-포르밀페닐)우레아;
4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(피리딘-2-일메틸)벤즈아미드;
1-(4-{4-[2-(1,3-디옥산-2-일)에틸]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
1-(4-{4-[2,5-비스(히드록시메틸)피롤리딘-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-{4-[2-(디메틸아미노)에톡시]페닐}벤즈아미드;
1-{4-[(4-벤질피페리딘-1-일)카르보닐]페닐}-3-[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;
4-({[4-(4-부틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸피페리딘-4-일)벤즈아미드;
1-(4-{4-[3-(디메틸아미노)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
1-[4-(4-{3-[(1-메틸에틸)아미노]프로필}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
1-{4-[4-모르폴린-4-일-6-(3-피롤리딘-1-일프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-(4-{4-[3-(4-메틸피페라진-1-일)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
1-{4-[4-(3-{[2-(디메틸아미노)에틸]아미노}프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-(3-히드록시프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-모르폴린-4-일-6-(3-옥소프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아;
4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]벤즈아미드;
1-[4-(4-메틸피페라진-1-일)페닐]-3-[4-(4-모르폴린-4-일-6-프로필-1,3,5-트리아진-2-일)페닐]우레아;
1-{4-[2-(디메틸아미노)에톡시]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-[4-(4-메틸피페라진-1-일)페닐]우레아;
1-[4-(4-메틸피페라진-1-일)페닐]-3-{4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-{4-[(3,3-디메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(1-메틸아제티딘-3-일)벤즈아미드;
메틸 4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트
N-[2-(디메틸아미노)에틸]-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
N-(1-메틸아제티딘-3-일)-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-피리딘-4-일벤즈아미드;
4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-피리딘-3-일벤즈아미드;
N-시클로부틸-4-[({4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-페닐피페리딘-1-일)카르보닐]페닐}우레아;
4-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(피리딘-4-일메틸)벤즈아미드;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;
1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-[4-(4-메틸피페라진-1-일)페닐]우레아;
메틸 4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;
1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-일)피리딘-3-일)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-((디메틸아미노)메틸)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)에톡시)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(피롤리딘-1-일)에톡시)페닐)우레아;
(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아;
(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-일)페닐)우레아;
1-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-((S)-3-메틸피페라진-1-일)페닐)우레아;
1-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-((R)-3-메틸피페라진-1-일)페닐)우레아;
1-(4-((3R,5S)-3,5-디메틸피페라진-1-일)페닐)-3-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(2-(디메틸아미노)에톡시)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(4-에틸피페라진-1-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(4-이소프로필피페라진-1-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
(R)-1-(4-(4-이소프로필피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-일)피리딘-3-일)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-일)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;
4-(3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레이도)-N,N-디메틸벤즈아미드;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피롤리딘-1-일메틸)페닐)우레아;
4-({[4-(4-{4-[(메틸카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
1-{4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;
3-({[4-(4-{4-[(메틸카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
1-메틸-3-[4-(4-모르폴린-4-일-6-{4-[(피리딘-3-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)페닐]우레아;
1-메틸-3-[4-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)페닐]우레아;
3-[({4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
4-[({4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-{4-[4-(3,5-디메틸모르폴린-4-일)-6-{4-[(메틸카르바모일)아미노]페닐}-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-메틸우레아;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리다진-4-일우레아;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(옥세탄-3-일옥시)-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-(4-이소프로필-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-피리미딘-5-일페닐)우레아;
1-(4-{4-[(2,2-디메톡시에틸)아미노]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-3-일우레아;
1-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-피리딘-4-일페닐)우레아;
1-(4-요오도페닐)-3-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;
1-[4-(4-아제티딘-1-일-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;
1-{4-[2-(디메틸아미노)피리미딘-5-일]페닐}-3-{4-[4-(1-메틸에틸)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
tert-부틸 3-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]아제티딘-1-카르복실레이트;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-니트로페닐)우레아;
1-(4-아미노페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
N-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-4-메틸피페라진-1-카르복스아미드;
4-(디메틸아미노)-N-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]피페리딘-1-카르복스아미드;
1-[2-(디메틸아미노)에틸]-3-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-1-메틸우레아;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-{[(2-피페리딘-1-일에틸)카르바모일]아미노}페닐)우레아;
N-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-4-메틸-1,4-디아제판-1-카르복스아미드;
N-[4-({[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)페닐]-4-에틸피페라진-1-카르복스아미드;
1-{4-[(디메틸카르바모일)아미노]페닐}-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아;
4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;
1-{4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
4-[({4-[4-(3,6-디히드로-2H-피란-4-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-[2-(디메틸아미노)에틸]벤즈아미드;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
N-[2-(디메틸아미노)에틸]-4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-(2-피롤리딘-1-일에틸)벤즈아미드;
4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-(2-피페리딘-1-일에틸)벤즈아미드;
1-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;
N-[2-(디메틸아미노)에틸]-N-메틸-4-{[(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
4-{[(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-피페리딘-1-일에틸)벤즈아미드;
4-{[(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-피롤리딘-1-일에틸)벤즈아미드;
1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-(4-{4-모르폴린-4-일-6-[(3S)-테트라히드로푸란-3-일옥시]-1,3,5-트리아진-2-일}페닐)우레아;
1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
4-[({4-[4-(2-메틸프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;
1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-[4-(4-메틸피페라진-1-일)페닐]우레아;
4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;
메틸 4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;
1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-피리딘-2-일피페라진-1-일)카르보닐]페닐}우레아;
1-{4-[4-(디메틸아미노)피페리딘-1-일]페닐}-3-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]우레아;
1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
메틸 4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
N-[2-(디메틸아미노)에틸]-N-메틸-4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
메틸 4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;
4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;
N-[2-(디메틸아미노)에틸]-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]우레아;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]우레아;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-[2-(디메틸아미노)에틸]벤즈아미드;
1-{4-[(4-이소프로필피페라진-1-일)카르보닐]페닐}-3-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]-N-(2-피롤리딘-1-일에틸)벤즈아미드;
4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;
N-(2-메톡시에틸)-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
N-(2-메톡시에틸)-4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피롤리딘-1-일에틸)벤즈아미드;
1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-[4-(피롤리딘-1-일카르보닐)페닐]우레아;
N-[3-(디메틸아미노)프로필]-4-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-[4-(피페리딘-1-일카르보닐)페닐]우레아;
N-[3-(디메틸아미노)프로필]-4-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
1-{4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}우레아;
메틸 4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;
N-(2-메톡시에틸)-4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
N-[2-(디메틸아미노)에틸]-4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-[2-(디메틸아미노)에틸]-N-메틸벤즈아미드;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-{4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
메틸 4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}우레아;
4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;
N-[3-(디메틸아미노)프로필]-4-[({4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-[4-(피롤리딘-1-일카르보닐)페닐]우레아;
N-[2-(디메틸아미노)에틸]-4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
N-(2-메톡시에틸)-4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(2-티에닐)-1,3,5-트리아진-2-일]페닐}우레아;
1-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-{3-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
3-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조산;
메틸 3-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;
1-(3-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-{4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
N-[2-(디메틸아미노)에틸]-N-메틸-3-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
메틸 3-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
메틸 3-({[4-(4-모르폴린-4-일-6-티오펜-2-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
N-[2-(디메틸아미노)에틸]-3-[({4-[4-(4-메틸페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-모르폴린-4-일-6-(1,4-옥사제판-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
3-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;
메틸 3-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{3-[(4-피리딘-2-일피페라진-1-일)카르보닐]페닐}우레아;
N-[2-(디메틸아미노)에틸]-3-({[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;
1-[4-(4-에틸-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{3-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
3-({[4-(4-모르폴린-4-일-6-페닐-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;
메틸 4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
1-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;
메틸 4-({[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조에이트;
1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;
1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;
4-({[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤조산;
1-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;
1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;
N-[2-(디메틸아미노)에틸]-N-메틸-4-({[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
N-[2-(디메틸아미노)에틸]-N-메틸-4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]우레아;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
N-[3-(디메틸아미노)프로필]-4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
N-(2-메톡시에틸)-4-({[4-(4-모르폴린-4-일-6-피페리딘-1-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
1-[4-(4-모르폴린-4-일-6-피롤리딘-1-일-1,3,5-트리아진-2-일)페닐]-3-[4-(피롤리딘-1-일카르보닐)페닐]우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;
메틸 4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)우레아;
1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;
4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;
1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;
N-[3-(디메틸아미노)프로필]-4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-피롤리딘-1-일에틸)벤즈아미드;
1-(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(디프로필아미노)피페리딘-1-일]카르보닐}페닐)우레아;
1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)우레아;
4-{[(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;
1-{4-[(4-부틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)우레아;
메틸 4-{[(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-부틸피페라진-1-일)카르보닐]페닐}우레아;
1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(2-메틸프로필)피페라진-1-일]카르보닐}페닐)우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸프로필)피페라진-1-일]카르보닐}페닐)우레아;
4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-[2-(4-메틸피페라진-1-일)에틸]벤즈아미드;
N-[2-(디메틸아미노)에틸]-4-{[(4-{4-[(3R)-3-메틸모르폴린-4-일]-6-[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-피롤리딘-1-일에틸)벤즈아미드;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-프로필피페리딘-1-일)카르보닐]페닐}우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-[4-(피페리딘-1-일카르보닐)페닐]우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-프로필피페라진-1-일)카르보닐]페닐}우레아;
4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}-N-(2-메톡시에틸)벤즈아미드;
1-{4-[4-모르폴린-4-일-6-(4-트리시클로[3.3.1.13,7]데크-1-일피페라진-1-일)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
메틸 4-{[(4-{4-[4-(디메틸카르바모일)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;
N,N-디메틸-4-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)피페라진-1-카르복스아미드;
N,N-디메틸-4-(4-{4-[({4-[(4-메틸피페라진-1-일)카르보닐]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)피페라진-1-카르복스아미드;
N,N-디메틸-4-{4-모르폴린-4-일-6-[4-({[4-(피리다진-4-일카르바모일)페닐]카르바모일}아미노)페닐]-1,3,5-트리아진-2-일}피페라진-1-카르복스아미드;
N,N-디메틸-4-(4-모르폴린-4-일-6-{4-[({4-[(4-프로필피페리딘-1-일)카르보닐]페닐}카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)피페라진-1-카르복스아미드;
4-{[(4-{4-[4-(디메틸카르바모일)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;
4-(4-{4-[({4-[(2-메톡시에틸)카르바모일]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)-N,N-디메틸피페라진-1-카르복스아미드;
4-[4-(4-{[(4-{[2-(디메틸아미노)에틸](메틸)카르바모일}페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]-N,N-디메틸피페라진-1-카르복스아미드;
4-(4-{4-[({4-[(4-에틸피페라진-1-일)카르보닐]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)-N,N-디메틸피페라진-1-카르복스아미드;
1-(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
메틸 4-{[(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;
4-{[(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;
N-[3-(디메틸아미노)프로필]-4-{[(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
N-[2-(디메틸아미노)에틸]-4-{[(4-{4-[4-(에틸술포닐)피페라진-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
4-{[(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;
메틸 4-{[(4-{4-[4-(아세틸아미노)피페리딘-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;
1-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
N-[1-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)피페리딘-4-일]아세트아미드;
4-{[(4-{4-[4-(아세틸아미노)피페리딘-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;
N-[2-(디메틸아미노)에틸]-4-{[(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
N-{1-[(4-{[(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}페닐)카르보닐]피페리딘-4-일}아세트아미드;
1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;
1-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[(3S)-3-메틸모르폴린-4-일]카르보닐}페닐)우레아;
1-{4-[(4-부틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;
1-(4-{4-[(4-메틸피페라진-1-일)아미노]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-페닐우레아;
1-(4-{4-[(1-메틸피페리딘-4-일)옥시]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
1-{4-[4-모르폴린-4-일-6-(피페리딘-4-일옥시)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
에틸 4-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]피페리딘-1-카르복실레이트;
N-에틸-4-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]피페리딘-1-카르복스아미드;
tert-부틸 4-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]피페리딘-1-카르복실레이트;
4-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]피페리딘-1-술폰아미드;
1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-3-일우레아;
1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-페닐우레아;
1-[4-(디메틸아미노)페닐]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-시아노페닐)-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-(2-메틸피리딘-4-일)우레아;
1-[2-(디메틸아미노)에틸]-3-{4-[4-(1,4-디옥사-8-아자스피로[4.5]데크-8-일)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}우레아;
1-[4-(4-모르폴린-4-일-6-퀴놀린-3-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
1-{4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
메틸 4-[({4-[4-(2-메톡시에톡시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤조에이트;
1-(4-{4-모르폴린-4-일-6-[2-(피리딘-4-일아미노)에틸]-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸벤즈아미드;
N-[2-(디메틸아미노)에틸]-4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)벤즈아미드;
4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-메틸-N-[2-(메틸아미노)에틸]벤즈아미드;
1-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-{4-[(3,3-디메틸피페라진-1-일)카르보닐]페닐}-3-[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
4-({[4-(4-메톡시-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]카르바모일}아미노)-N-(2-피페리딘-1-일에틸)벤즈아미드;
1-(4-{4-[2,5-비스(히드록시메틸)피롤리딘-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
1-(4-{4-[2-(1,3-디옥산-2-일)에틸]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
1-(4-{4-[3-(디메틸아미노)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
1-[4-(4-{3-[(1-메틸에틸)아미노]프로필}-6-모르폴린-4-일-1,3,5-트리아진-2-일)페닐]-3-피리딘-4-일우레아;
1-{4-[4-모르폴린-4-일-6-(3-피롤리딘-1-일프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-(4-{4-[3-(4-메틸피페라진-1-일)프로필]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-피리딘-4-일우레아;
1-{4-[4-(3-{[2-(디메틸아미노)에틸]아미노}프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-(3-히드록시프로필)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
1-{4-[4-모르폴린-4-일-6-(3-옥소프로필)-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
N-(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)벤젠술폰아미드;
N-{4-[4-({[4-(4-메틸피페라진-1-일)페닐]카르바모일}아미노)페닐]-6-모르폴린-4-일-1,3,5-트리아진-2-일}벤젠술폰아미드;
N-(4-{4-[({4-[2-(디메틸아미노)에톡시]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)벤젠술폰아미드;
N-(4-{4-[({4-[(4-메틸피페라진-1-일)카르보닐]페닐}카르바모일)아미노]페닐}-6-모르폴린-4-일-1,3,5-트리아진-2-일)벤젠술폰아미드;
N-{4-모르폴린-4-일-6-[4-({[4-(피페라진-1-일카르보닐)페닐]카르바모일}아미노)페닐]-1,3,5-트리아진-2-일}벤젠술폰아미드;
N-[4-(4-{[(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)카르바모일]아미노}페닐)-6-모르폴린-4-일-1,3,5-트리아진-2-일]벤젠술폰아미드;
N-[2-(디메틸아미노)에틸]-N-메틸-4-{[(4-{4-모르폴린-4-일-6-[(페닐술포닐)아미노]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
N-[2-(디메틸아미노)에틸]-4-{[(4-{4-모르폴린-4-일-6-[(페닐술포닐)아미노]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
메틸 4-{[(4-{4-모르폴린-4-일-6-[(페닐술포닐)아미노]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조에이트;
4-{[(4-{4-모르폴린-4-일-6-[(페닐술포닐)아미노]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤조산;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-[4-(6-모르폴린-4-일-4-옥소-4,5-디히드로-1,3,5-트리아진-2-일)페닐]우레아;
1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필-2-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-시클로부틸-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필-3-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(3,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-이소프로필-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-이소프로필-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(3,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(2-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(3,3-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(3,3-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(3,3,4-트리메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4,6-디모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3,3,4-트리메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-이소프로필-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-이소프로필-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(3,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(3,3,4-트리메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(3,3-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(2,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-이소프로필-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸-2-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(4-이소프로필-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(3,4-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-시클로부틸-3-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(3,3-디메틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3,3,4-트리메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-시클로부틸피페라진-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(2-메틸모르폴리노)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아;
1-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(퀴누클리딘-4-일)페닐)우레아;
1-(4-(4-시클로프로필피페라진-1-일)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(시클로프로필메틸)피페라진-1-일)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아;
1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-일)페닐)우레아;
1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-시클로프로필피페라진-1-카르보닐)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(시클로프로필메틸)피페라진-1-카르보닐)페닐)-3-(4-(4-((2R,5S)-2,5-디메틸피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-일)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-일)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(퀴누클리딘-4-일)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-시클로프로필피페라진-1-일)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(시클로프로필메틸)피페라진-1-일)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-일)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-일)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-시클로프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-((2S,5R)-2,5-비스(히드록시메틸)피롤리딘-1-일)-6-((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(시클로프로필메틸)피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
N-(2-(메틸아미노)에틸)-4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
N-메틸-N-(2-(메틸아미노)에틸)-4-(3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-((R)-3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-메틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-에틸피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-이소프로필피페라진-1-카르보닐)페닐)-3-(4-(4-모르폴리노-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
4-(3-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-에틸피페라진-1-카르보닐)페닐)-3-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-이소프로필피페라진-1-카르보닐)페닐)-3-(4-(4-((S)-3-메틸모르폴리노)-6-(테트라히드로푸란-3-일옥시)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-클로로페닐)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-플루오로페닐)우레아;
메틸 4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조에이트;
4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산;
4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)벤즈아미드;
4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)-N-메틸벤즈아미드;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)우레아;
4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레아;
1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-n-프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-클로로페닐)-3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-플루오로페닐)-3-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(4-메틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-n-프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-클로로페닐)-3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-플루오로페닐)-3-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(4-에틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-n-프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
N-(2-(디메틸아미노)에틸)-4-(3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
N-(2-(디메틸아미노)에틸)-N-메틸-4-(3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-클로로페닐)-3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-플루오로페닐)-3-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(4-프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
1-(4-(4-(4-이소프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-(4-이소프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(4-이소프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(4-이소프로필-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-클로로페닐)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-플루오로페닐)우레아;
메틸-4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조에이트;
4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산;
4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)벤즈아미드;
4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)-N-(2-(디메틸아미노)에틸)-N-메틸벤즈아미드;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)우레아;
4-(3-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-n-프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-아세틸-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레아;
1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-에틸피페라진-1-카르보닐)페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레아;
1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-클로로페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-플루오로페닐)-3-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-(4-이소부티릴-1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
tert-부틸 4-(4-(4-(3-(4-(메톡시카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복실레이트;
메틸 4-(3-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조에이트;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-클로로페닐)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-플루오로페닐)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(1,4-디아제판-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
N-메틸-4-(4-모르폴리노-6-(4-(3-페닐우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드 (M+H) 532.2;
4-(4-(4-(3-(4-클로로페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-플루오로페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-(2-(디메틸아미노)에틸카르바모일)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-((2-(디메틸아미노)에틸)(메틸)카르바모일)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-카르바모일페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;
N-메틸-4-(4-모르폴리노-6-(4-(3-(4-(피페라진-1-카르보닐)페닐)우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;
N-메틸-4-(4-(4-(3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-메틸-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-이소프로필-1,4-디아제판-1-카르복스아미드;
N-이소프로필-4-(4-(4-(3-(4-(4-이소프로필피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;
4-(4-(4-(3-(4-(4-에틸피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-N-이소프로필-1,4-디아제판-1-카르복스아미드;
N-이소프로필-4-(4-(4-(3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레이도)페닐)-6-모르폴리노-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;
N-이소프로필-4-(4-모르폴리노-6-(4-(3-(4-(피페라진-1-카르보닐)페닐)우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;
N-이소프로필-4-(4-모르폴리노-6-(4-(3-피리딘-4-일우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;
N-이소프로필-4-(4-모르폴리노-6-(4-(3-피리다진-4-일우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;
N-이소프로필-4-(4-모르폴리노-6-(4-(3-피리미딘-5-일우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;
N-이소프로필-4-(4-모르폴리노-6-(4-(3-피리딘-3-일우레이도)페닐)-1,3,5-트리아진-2-일)-1,4-디아제판-1-카르복스아미드;
1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
1-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-클로로페닐)-3-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-플루오로페닐)-3-(4-(4-모르폴리노-6-(1H-피라졸-1-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-클로로페닐)-3-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-플루오로페닐)-3-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(2-메틸-1H-이미다졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
1-(4-아세틸페닐)-3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-일)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-(디메틸아미노)아세틸)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-모르폴리노아세틸)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-히드록시아세틸)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(메톡시메틸)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-메톡시에틸)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(1-히드록시에틸)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-히드록시프로판-2-일)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-히드록시프로필)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-히드록시-2-메틸프로필)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)우레아;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(4-시아노페닐)우레아;
4-(3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레이도)-N-메틸벤즈아미드;
4-(3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레이도)-N,N-디메틸벤즈아미드;
4-(3-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(4,6-비스((R)-3-메틸모르폴리노)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-카르보닐)피리딘-3-일)우레아;
(R)-1-(4-((디메틸아미노)메틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
(R)-1-(4-아세틸페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(2-(디메틸아미노)아세틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(4-(2-모르폴리노아세틸)페닐)우레아;
(R)-1-(4-(2-히드록시아세틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(메톡시메틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(2-메톡시에틸)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(1-히드록시에틸)페닐)-3-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(2-히드록시프로판-2-일)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(2-히드록시프로필)페닐)-3-(4-(4-((R)-3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(2-히드록시-2-메틸프로필)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-1-(4-시아노페닐)-3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레아;
(R)-N-메틸-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
(R)-N,N-디메틸-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
(R)-4-(3-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
(R)-1-(4-(4-(3-메틸모르폴리노)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일)페닐)-3-(6-(4-메틸피페라진-1-카르보닐)피리딘-3-일)우레아;
1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리미딘-5-일)우레아;
1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-3-일)우레아;
1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리딘-4-일)우레아;
1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(피리다진-4-일)우레아;
1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-페닐우레아;
1-(4-클로로페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-플루오로페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
메틸 4-(3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조에이트;
4-(3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤조산;
4-(3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레이도)벤즈아미드;
1-(4-(3-(디메틸아미노)피롤리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)-3-(4-(4-메틸피페라진-1-카르보닐)페닐)우레아;
1-(4-(4-에틸피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-이소프로필피페라진-1-카르보닐)페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-(4-(4-(디메틸아미노)피페리딘-1-카르보닐)페닐)-3-(4-(4-(3-메틸-1H-피라졸-1-일)-6-모르폴리노-1,3,5-트리아진-2-일)페닐)우레아;
1-{4-[(4-부틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;
1-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)우레아;
1-{4-[(4-에틸피페라진-1-일)카르보닐]페닐}-3-(4-{4-[4-(1-메틸에틸)-1,4-디아제판-1-일]-6-모르폴린-4-일-1,3,5-트리아진-2-일}페닐)우레아;
1-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아;
1-(4-{[4-(1-메틸에틸)피페라진-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
N-[2-(디메틸아미노)에틸]-N-메틸-4-[({4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}카르바모일)아미노]벤즈아미드;
1-{4-[4-(아제티딘-3-일옥시)-6-모르폴린-4-일-1,3,5-트리아진-2-일]페닐}-3-피리딘-4-일우레아;
N-(1-메틸에틸)-3-[(4-모르폴린-4-일-6-{4-[(피리딘-4-일카르바모일)아미노]페닐}-1,3,5-트리아진-2-일)옥시]아제티딘-1-카르복스아미드;
N-{1-[(4-{[(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}페닐)카르보닐]피페리딘-4-일}아세트아미드;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(1-메틸에틸)-1,4-디아제판-1-일]카르보닐}페닐)우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-[4-(3-옥사-8-아자비시클로[3.2.1]옥트-8-일카르보닐)페닐]우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-시아노피페리딘-1-일)카르보닐]페닐}우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)우레아;
1-(4-{4,6-비스[(3S)-3-메틸모르폴린-4-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)우레아;
1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;
1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;
1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-{4-[(2-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)-3-[4-(피페라진-1-일카르보닐)페닐]우레아;
1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;
1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-{4-[(3,3,4-트리메틸피페라진-1-일)카르보닐]페닐}우레아;
1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-(4-{[(3R)-3-메틸피페라진-1-일]카르보닐}페닐)우레아;
1-(4-{[(3R)-3,4-디메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-{[(3R)-4-시클로부틸-3-메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-(4-{[(3R)-3-메틸-4-(프로판-2-일)피페라진-1-일]카르보닐}페닐)우레아;
1-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}-3-(4-{[(3S)-3-메틸피페라진-1-일]카르보닐}페닐)우레아;
N-[2-(디메틸아미노)에틸]-N-메틸-4-{[(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
1-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)-3-{4-[(4-메틸피페라진-1-일)카르보닐]페닐}우레아;
1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-(4-{4-[(3S)-3-메틸모르폴린-4-일]-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;
N-[3-(디메틸아미노)프로필]-4-{[(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
N-[2-(디메틸아미노)에틸]-N-메틸-4-{[(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
1-[4-(모르폴린-4-일카르보닐)페닐]-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;
N-(2-메톡시에틸)-4-{[(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)카르바모일]아미노}벤즈아미드;
1-[4-(1,4-디아제판-1-일카르보닐)페닐]-3-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)우레아;
1-(4-{4-(모르폴린-4-일)-6-[4-(프로판-2-일)-1,4-디아제판-1-일]-1,3,5-트리아진-2-일}페닐)-3-(4-{[4-(프로판-2-일)-1,4-디아제판-1-일]카르보닐}페닐)우레아;
1-(4-{[(3S)-4-시클로부틸-3-메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-{[(3S)-3,4-디메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4,6-디(모르폴린-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
1-{4-[4-(모르폴린-4-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}-3-{4-[(3,3,4-트리메틸피페라진-1-일)카르보닐]페닐}우레아;
1-(4-{[(3S)-3,4-디메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4-(모르폴린-4-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-{[(3S)-3-메틸피페라진-1-일]카르보닐}페닐)-3-{4-[4-(모르폴린-4-일)-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아;
1-(4-{[(3R)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아; 및
1-(4-{[(3S)-3-(디메틸아미노)피롤리딘-1-일]카르보닐}페닐)-3-{4-[4-모르폴린-4-일-6-(테트라히드로-2H-피란-4-일)-1,3,5-트리아진-2-일]페닐}우레아
로 이루어진 군으로부터 선택된 화합물 또는 그의 제약상 허용되는 염.1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-3-ylurea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-phenylurea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-thiophen-2-ylurea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-methylphenyl) urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-fluorophenyl) urea;
1- (2,4-dimethoxyphenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -urea;
1- (4-chlorophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-methoxyphenyl) urea;
(4-chlorophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea;
(2,4-difluorophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-ethylurea;
tert-butyl 3-{[4- (4-{[(4-fluorophenyl) carbamoyl] amino} phenyl) -6-morpholin-4-yl-1,3,5-triazine-2- General] amino} azetidine-1-carboxylate;
tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(phenylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) amino] azetidine -1-carboxylate;
tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-3-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) Amino] azetidine-1-carboxylate;
tert-butyl 3-{[4- (4-{[(4-methylphenyl) carbamoyl] amino} phenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Amino} azetidine-1-carboxylate;
1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-phenylurea;
1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-3-yl Urea;
1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-fluoro Phenyl) urea;
1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-methylphenyl) Urea;
tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) Amino] azetidine-1-carboxylate;
1- {4- [4- (azetidin-3-ylamino) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-yl Urea;
1- [2- (dimethylamino) ethyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (2-methylpyridin-4-yl) urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (2-hydroxyethyl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4-hydroxyphenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (1-hydroxyethyl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (trifluoromethyl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-hydroxyphenyl) urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [5- (trifluoromethyl) pyridin-2-yl ] Urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4- [2,2,2-trifluoro- 1-hydroxy-1- (trifluoromethyl) ethyl] phenyl} urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [3- (1-hydroxyethyl) phenyl] urea;
Methyl 4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;
1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-pyridine -4-ylurea;
1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-phenyl Urea;
1- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-pyridine -3-ylurea;
1- [4- (hydroxymethyl) phenyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5- Triazin-2-yl] phenyl} urea;
1- (2-methylpyridin-4-yl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5- Triazin-2-yl] phenyl} urea;
1- [2- (methylamino) ethyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-tri Azin-2-yl] phenyl} urea;
1- (3-acetylphenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-triazine-2 -Yl] phenyl} urea;
1- [4- (dimethylamino) phenyl] -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yloxy) -1,3,5-tri Azin-2-yl] phenyl} urea;
4- [3- {4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl} ureido] benzoic acid;
N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzamide ;
N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzamide HCl salts;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) Urea;
4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N-methylbenzamide;
N- (2- (dimethylamino) ethyl) -4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N Methylbenzamide;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-morpholinopiperidine-1-carbonyl) Phenyl) urea;
4- (3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N- (quinuclidin-3-yl) benzamide ;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4- (pyrrolidin-1-yl) piperi Din-1-carbonyl) phenyl) urea;
1- (4- (1,4'-bipiperidine-1'-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazine-2- Yl) phenyl) urea;
1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazine-2- Yl) phenyl) urea;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (piperazin-1-carbonyl) phenyl) urea;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (2- (pyridin-2-yl) acetyl) phenyl) Urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (1-hydroxyethyl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (2-methylpyridin-4-yl) urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (trifluoromethyl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4- [2,2,2-trifluoro- 1-hydroxy-1- (trifluoromethyl) ethyl] phenyl} urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [5- (trifluoromethyl) pyridin-2-yl ] Urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [3- (1-hydroxyethyl) phenyl] urea;
1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -Pyridin-4-ylurea;
1- [4- (2-hydroxyethyl) phenyl] -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1, 3,5-triazin-2-yl} phenyl) urea;
1- [4- (2-hydroxymethyl) phenyl] -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1, 3,5-triazin-2-yl} phenyl) urea;
1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -(2-methylpyridin-4-yl) urea;
1- [4- (1-hydroxyethyl) phenyl] -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1, 3,5-triazin-2-yl} phenyl) urea;
1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
Methyl 4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} -amino) benzoate;
1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin- 1-yl) carbonyl] phenyl} urea;
4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1- Methylpiperidin-4-yl) benzamide;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (1-methylpiperidin-4-yl) urea;
1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -(1-methylpiperidin-4-yl) urea;
1- {4- [4- (3,6-Dihydro-2H-pyran-4-yl) -6-morpholin-4-yl- [1,3,5] triazin-2-yl] -phenyl } -3-pyridin-4-yl-urea;
1- {4- [4-morpholin-4-yl-6- (tetrahydro-pyran-4-yl)-[1,3,5] triazin-2-yl] -phenyl} -3-pyridine- 4-yl-urea;
3-({4-morpholin-4-yl-6- [4- (3-pyridin-4-yl-ureido) -phenyl]-[1,3,5] triazin-2-ylamino}- Methyl) -azetidine-1-carboxylic acid tert-butyl ester;
1- (4- {4-[(azetidin-3-ylmethyl) -amino] -6-morpholin-4-yl- [1,3,5] triazin-2-yl} -phenyl) -3 -Pyridin-4-yl-urea;
1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-pyridin-4-ylurea;
1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-pyridin-3-ylurea;
1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-phenylurea;
1- [4- (dimethylamino) phenyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;
1- (4-cyanophenyl) -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl-1 , 3,5-triazin-2-yl] phenyl} urea;
1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3- (2-methylpyridin-4-yl) urea;
1- [2- (dimethylamino) ethyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;
1- [4- (4-morpholin-4-yl-6-quinolin-3-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
1- [4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
Methyl 4-({[4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate ;
1- [4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin- 1-yl) carbonyl] phenyl} urea;
4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1- Methylpiperidin-4-yl) benzamide;
4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (2-piperidine -1-ylethyl) benzamide;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (morpholin-4-ylcarbonyl) phenyl ] Urea;
1- [4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
4-({[4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;
1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl}- 3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;
4-({[4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1-methylpy Ferridin-4-yl) benzamide;
N- [2- (dimethylamino) ethyl] -N-methyl-4-({[4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) Phenyl] carbamoyl} amino) benzamide;
1- [4- (4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;
1- (4-{[3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5 -Triazin-2-yl) phenyl] urea;
1- [4-({4- [2- (dimethylamino) ethyl] piperazin-1-yl} carbonyl) phenyl] -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-pyrrolidin-1-ylpy Ferridin-1-yl) carbonyl] phenyl} urea;
4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] Carbamoyl} amino) -N-methylbenzamide;
1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-isopropoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] Carbamoyl} amino) benzamide;
4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;
4-({[4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid; mp 204 ° C;
1- [4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methyl Piperazin-1-yl) carbonyl] phenyl} urea; mp 170 [deg.] C;
4-({[4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [2- (dimethylamino) ethyl] -N-methylbenzamide;
4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [2- (dimethyl Amino) ethyl] -N-methylbenzamide;
1- {4- [4- (1-ethoxyvinyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
1- {4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea ;
1- [4- (4-acetyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
Methyl 4-[({4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] Benzoate;
1- {4- [4- (1-hydroxyethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
Methyl 4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Phenyl} carbamoyl) amino] benzoate;
4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] benzoic acid;
1- (4- {4-morpholin-4-yl-6- [2- (pyridin-4-ylamino) ethyl] -1,3,5-triazin-2-yl} phenyl) -3-pyridine -4-ylurea;
4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [2- (dimethyl Amino) ethyl] benzamide;
1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;
1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) benzamide;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4-ethyl-6-morpholin-4-yl-1,3, 5-triazin-2-yl) phenyl] urea;
1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (hydroxymethyl) phenyl] urea;
4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] -N- [2- (dimethylamino) ethyl] -N-methylbenzamide;
1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-{[4- (dimethylamino) piperi Din-1-yl] carbonyl} phenyl) urea;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) -N-methylbenzamide;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) -N-methylbenzamide;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) benzamide;
4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N-methyl-N- [2- (methylamino) ethyl] benzamide;
1- [4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1 -Yl) carbonyl] phenyl} urea;
1- {4-[(3,3-dimethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-methoxy-6-morpholin-4-yl-1,3,5 -Triazin-2-yl) phenyl] urea;
4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (2-py Ferridin-1-ylethyl) benzamide;
4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [4- (4 -Methylpiperazin-1-yl) phenyl] benzamide;
1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4-({[2- (dimethylamino) ethyl ] Amino} methyl) phenyl] urea;
4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- [4- (4 -Methylpiperazin-1-yl) phenyl] benzamide;
1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) methyl] phenyl} urea;
1- [4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-formylphenyl) urea;
4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (pyridin-2-yl Methyl) benzamide;
1- (4- {4- [2- (1,3-dioxan-2-yl) ethyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea;
1- (4- {4- [2,5-bis (hydroxymethyl) pyrrolidin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} Phenyl) -3-pyridin-4-ylurea;
4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- {4- [2 -(Dimethylamino) ethoxy] phenyl} benzamide;
1- {4-[(4-benzylpiperidin-1-yl) carbonyl] phenyl} -3- [4- (4-butyl-6-morpholin-4-yl-1,3,5-tri Azin-2-yl) phenyl] urea;
4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1-methylpy Ferridin-4-yl) benzamide;
4-({[4- (4-butyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1-methylpy Ferridin-4-yl) benzamide;
1- (4- {4- [3- (dimethylamino) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-yl Urea;
1- [4- (4- {3-[(1-methylethyl) amino] propyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- Pyridin-4-ylurea;
1- {4- [4-morpholin-4-yl-6- (3-pyrrolidin-1-ylpropyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridine- 4-ylurea;
1- (4- {4- [3- (4-methylpiperazin-1-yl) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl)- 3-pyridin-4-ylurea;
1- {4- [4- (3-{[2- (dimethylamino) ethyl] amino} propyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
1- {4- [4- (3-hydroxypropyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
1- {4- [4-morpholin-4-yl-6- (3-oxopropyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl}- 3- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) urea;
4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] -N- [2- (dimethylamino) ethyl] benzamide;
1- [4- (4-methylpiperazin-1-yl) phenyl] -3- [4- (4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-yl ) Phenyl] urea;
1- {4- [2- (dimethylamino) ethoxy] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) Phenyl] urea;
1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (4-methylpiperazin-1-yl ) Phenyl] urea;
1- [4- (4-methylpiperazin-1-yl) phenyl] -3- {4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3,5-tri Azin-2-yl] phenyl} urea;
1- {4-[(3,3-dimethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3,5- Triazin-2-yl) phenyl] urea;
4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (1-methylase Thidin-3-yl) benzamide;
Methyl 4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate
N- [2- (dimethylamino) ethyl] -4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl ] Phenyl} carbamoyl) amino] benzamide;
N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazine -2-yl] phenyl} carbamoyl) amino] benzamide;
N- (1-methylazetidin-3-yl) -4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazine-2 -Yl] phenyl} carbamoyl) amino] benzamide;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4- (1-methylethyl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;
4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] -N- Pyridin-4-ylbenzamide;
4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] -N- Pyridin-3-ylbenzamide;
N-cyclobutyl-4-[({4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) Amino] benzamide;
1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-phenylpiperidine-1 -Yl) carbonyl] phenyl} urea;
4-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (pyridine-4- Monomethyl) benzamide;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3 , 5-triazin-2-yl] phenyl} urea;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4- (2-methylpropyl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;
N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3,5-triazine -2-yl] phenyl} carbamoyl) amino] benzamide;
1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- {4-[(4-methylpipepe Razin-1-yl) carbonyl] phenyl} urea;
N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;
1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3, 5-triazin-2-yl] phenyl} urea;
1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazine -2-yl) phenyl] urea;
4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;
1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- [4- (4-methylpiperazin -1-yl) phenyl] urea;
Methyl 4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate;
1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazine -2-yl) phenyl] urea;
1- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) urea ;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-3-yl) urea ;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpipepe Razin-1-yl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (6- (4-methylpipepe Razin-1-yl) pyridin-3-yl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4-((dimethylamino) Methyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2- (dimethyl Amino) ethoxy) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2- (pi Ralidin-1-yl) ethoxy) phenyl) urea;
(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (pyridin-3-yl) urea;
(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea;
(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4- (piperazin-1-yl) phenyl) urea;
1- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4-((S) -3-methylpiperazin-1-yl) phenyl) urea;
1- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4-((R) -3-methylpiperazin-1-yl) phenyl) urea;
1- (4-((3R, 5S) -3,5-dimethylpiperazin-1-yl) phenyl) -3- (4- (4-((R) -3-methylmorpholino) -6- (Tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (2- (dimethylamino) ethoxy) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4 -Yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (4-ethylpiperazin-1-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran- 4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (4-isopropylpiperazin-1-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran -4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro- 2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
(R) -1- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (6- (4-methylpiperazin-1-yl) pyridin-3-yl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-ethylpipepe Razin-1-yl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropyl Piperazin-1-yl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethyl Amino) piperidin-1-yl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpipepe Razin-1-carbonyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropyl Piperazine-1-carbonyl) phenyl) urea;
4- (3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) ureido) -N, N- Dimethylbenzamide;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (pyrrolidine- 1-ylmethyl) phenyl) urea;
4-({[4- (4- {4-[(methylcarbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) benzamide;
1- {4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-triazine-2- Il] phenyl} -3-pyridin-3-ylurea;
3-({[4- (4- {4-[(methylcarbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) benzamide;
1-methyl-3- [4- (4-morpholin-4-yl-6- {4-[(pyridin-3-ylcarbamoyl) amino] phenyl} -1,3,5-triazine-2 -Yl) phenyl] urea;
1-methyl-3- [4- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazine-2 -Yl) phenyl] urea;
3-[({4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;
4-[({4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;
1- {4- [4- (3,5-dimethylmorpholin-4-yl) -6- {4-[(methylcarbamoyl) amino] phenyl} -1,3,5-triazine-2- Il] phenyl} -3-pyridin-4-ylurea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-methylurea;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4-morpholin-4-yl-6-[(3S) -tetrahydrofuran-3 -Yloxy] -1,3,5-triazin-2-yl} phenyl) urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridazin-4-ylurea;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (oxetan-3-yloxy)- 1,3,5-triazin-2-yl] phenyl} urea;
1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;
1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;
1- [4- (4-isopropyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1 -Yl) carbonyl] phenyl} urea;
1- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-pyrimidine-5- Phenyl) urea;
1- (4- {4-[(2,2-dimethoxyethyl) amino] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridine- 3-ylurea;
1- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-pyridin-4-yl Phenyl) urea;
1- (4-iodophenyl) -3- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} urea ;
1- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- (4-{[4- ( 1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;
1- [4- (4-azetidin-1-yl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-{[4- ( 1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;
1- {4- [2- (dimethylamino) pyrimidin-5-yl] phenyl} -3- {4- [4- (1-methylethyl) -6-morpholin-4-yl-1,3, 5-triazin-2-yl] phenyl} urea;
tert-butyl 3-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) Oxy] azetidine-1-carboxylate;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5 -Triazin-2-yl) phenyl] urea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-nitrophenyl) urea;
1- (4-aminophenyl) -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] urea;
N- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) phenyl] -4-methyl Piperazine-1-carboxamide;
4- (dimethylamino) -N- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino ) Phenyl] piperidine-1-carboxamide;
1- [2- (dimethylamino) ethyl] -3- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] Carbamoyl} amino) phenyl] -1-methylurea;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-{[(2-piperidin-1- One ethyl) carbamoyl] amino} phenyl) urea;
N- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) phenyl] -4-methyl -1,4-diazepane-1-carboxamide;
N- [4-({[4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) phenyl] -4-ethyl Piperazine-1-carboxamide;
1- {4-[(dimethylcarbamoyl) amino] phenyl} -3- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] Urea;
1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl}- 3- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) urea;
4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] -N- [2- (dimethylamino) ethyl] -N-methylbenzamide;
1- {4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl}- 3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;
4-[({4- [4- (3,6-dihydro-2H-pyran-4-yl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] -N- [2- (dimethylamino) ethyl] benzamide;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;
N- [2- (dimethylamino) ethyl] -4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1,3,5- Triazin-2-yl] phenyl} carbamoyl) amino] benzamide;
4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} carbamoyl ) Amino] -N- (2-pyrrolidin-1-ylethyl) benzamide;
4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} carbamoyl ) Amino] -N- (2-piperidin-1-ylethyl) benzamide;
1- [4- (4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- (4-{[4- (1-methylethyl) pipe Razin-1-yl] carbonyl} phenyl) urea;
N- [2- (dimethylamino) ethyl] -N-methyl-4-{[(4- {4-morpholin-4-yl-6-[(3S) -tetrahydrofuran-3-yloxy]- 1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
4-{[(4- {4-morpholin-4-yl-6-[(3S) -tetrahydrofuran-3-yloxy] -1,3,5-triazin-2-yl} phenyl) carr Barmoyl] amino} -N- (2-piperidin-1-ylethyl) benzamide;
4-{[(4- {4-morpholin-4-yl-6-[(3S) -tetrahydrofuran-3-yloxy] -1,3,5-triazin-2-yl} phenyl) carr Barmoyl] amino} -N- (2-pyrrolidin-1-ylethyl) benzamide;
1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- (4- {4-morpholin-4-yl-6-[(3S)- Tetrahydrofuran-3-yloxy] -1,3,5-triazin-2-yl} phenyl) urea;
1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H -Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;
N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1, 3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide;
4-[({4- [4- (2-methylpropyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;
1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- [4- (4-methylpiperazin -1-yl) phenyl] urea;
4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;
Methyl 4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate;
1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazine -2-yl) phenyl] urea;
1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3, 5-triazin-2-yl] phenyl} urea;
N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;
1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- {4-[(4-methylpipepe Razin-1-yl) carbonyl] phenyl} urea;
1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-pyridin-2-ylpipepe Razin-1-yl) carbonyl] phenyl} urea;
1- {4- [4- (dimethylamino) piperidin-1-yl] phenyl} -3- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazine -2-yl) phenyl] urea;
1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;
1- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
Methyl 4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;
N- [2- (dimethylamino) ethyl] -N-methyl-4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) Phenyl] carbamoyl} amino) benzamide;
Methyl 4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino } Benzoate;
4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;
N- [2- (dimethylamino) ethyl] -4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Phenyl} carbamoyl) amino] benzamide;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazine -2-yl) phenyl] urea;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-phenyl-1,3, 5-triazin-2-yl) phenyl] urea;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) benzamide;
4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- [2- (dimethylamino) ethyl] benzamide;
1- {4-[(4-isopropylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3 , 5-triazin-2-yl] phenyl} urea;
4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] -N- ( 2-pyrrolidin-1-ylethyl) benzamide;
4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} Benzoic acid;
N- (2-methoxyethyl) -4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} Carbamoyl) amino] benzamide;
N- (2-methoxyethyl) -4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} Amino) benzamide;
4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (2-pyrroli Din-1-ylethyl) benzamide;
1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- [4- (pyrrolidine-1 -Ylcarbonyl) phenyl] urea;
N- [3- (dimethylamino) propyl] -4-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Phenyl} carbamoyl) amino] benzamide;
1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- [4- (piperidine-1 -Ylcarbonyl) phenyl] urea;
N- [3- (dimethylamino) propyl] -4-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) benzamide;
1- {4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (2-thienyl) -1,3 , 5-triazin-2-yl] phenyl} urea;
Methyl 4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate ;
N- (2-methoxyethyl) -4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl } Carbamoyl) amino] benzamide;
N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazine -2-yl] phenyl} carbamoyl) amino] benzamide;
N- [2- (dimethylamino) ethyl] -4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl ] Phenyl} carbamoyl) amino] benzamide;
4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- [2- (dimethylamino) ethyl] -N-methylbenzamide;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-methylpiperazin-1-yl) carbonyl] phenyl} urea;
1- {4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1,3,5-triazin-2-yl] phenyl} -3-pyridine- 4-ylurea;
Methyl 4-[({4- [4-morpholin-4-yl-6- (1,4-oxazapan-4-yl) -1,3,5-triazin-2-yl] phenyl} carba Moyl) amino] benzoate;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl] phenyl} urea;
4-[({4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1,3,5-triazin-2-yl] phenyl} carbamoyl ) Amino] benzoic acid;
N- [3- (dimethylamino) propyl] -4-[({4- [4-morpholin-4-yl-6- (2-thienyl) -1,3,5-triazin-2-yl ] Phenyl} carbamoyl) amino] benzamide;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- [4- (pi Rollidin-1-ylcarbonyl) phenyl] urea;
N- [2- (dimethylamino) ethyl] -4-[({4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1,3,5- Triazin-2-yl] phenyl} carbamoyl) amino] benzamide;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (1,4-oxazapan-4- Yl) -1,3,5-triazin-2-yl] phenyl} urea;
N- (2-methoxyethyl) -4-[({4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1,3,5-triazine -2-yl] phenyl} carbamoyl) amino] benzamide;
1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (2-thienyl) -1,3 , 5-triazin-2-yl] phenyl} urea;
1- {4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3- {3-[(4-methylpipepe Razin-1-yl) carbonyl] phenyl} urea;
3-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoic acid;
Methyl 3-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzoate;
1- (3-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- {4- [4- (4-methylphenyl) -6-morpholin-4-yl- 1,3,5-triazin-2-yl] phenyl} urea;
N- [2- (dimethylamino) ethyl] -N-methyl-3-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazine- 2-yl] phenyl} carbamoyl) amino] benzamide;
Methyl 3-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;
Methyl 3-({[4- (4-morpholin-4-yl-6-thiophen-2-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate ;
N- [2- (dimethylamino) ethyl] -3-[({4- [4- (4-methylphenyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] Phenyl} carbamoyl) amino] benzamide;
N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4-morpholin-4-yl-6- (1,4-oxazepan-4-yl) -1, 3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide;
3-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;
Methyl 3-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoate;
1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {3-[(4-pyridin-2-ylpipepe Razin-1-yl) carbonyl] phenyl} urea;
N- [2- (dimethylamino) ethyl] -3-({[4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carba Moyl} amino) -N-methylbenzamide;
1- [4- (4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {3-[(4-methylpiperazin-1- Yl) carbonyl] phenyl} urea;
3-({[4- (4-morpholin-4-yl-6-phenyl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;
Methyl 4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzo Eight;
1- [4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;
Methyl 4-({[4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzo Eight;
1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-piperidine-1 -Yl-1,3,5-triazin-2-yl) phenyl] urea;
1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-piperidin-1-yl-1, 3,5-triazin-2-yl) phenyl] urea;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-piperidin-1-yl-1, 3,5-triazin-2-yl) phenyl] urea;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-piperidine-1- Yl-1,3,5-triazin-2-yl) phenyl] urea;
4-({[4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) benzoic acid;
1- [4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazine-2- Yl) phenyl] carbamoyl} amino) benzamide;
1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-pyrrolidine-1- Yl-1,3,5-triazin-2-yl) phenyl] urea;
1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- [4- (4-morpholin-4-yl-6-pyrrolidine-1 -Yl-1,3,5-triazin-2-yl) phenyl] urea;
N- [2- (dimethylamino) ethyl] -N-methyl-4-({[4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-tri Azin-2-yl) phenyl] carbamoyl} amino) benzamide;
N- [2- (dimethylamino) ethyl] -N-methyl-4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-tri Azin-2-yl) phenyl] carbamoyl} amino) benzamide;
1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1, 3,5-triazin-2-yl) phenyl] urea;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1, 3,5-triazin-2-yl) phenyl] urea;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazine-2- Yl) phenyl] carbamoyl} amino) benzamide;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-yl Urea;
N- [3- (dimethylamino) propyl] -4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazine-2- Yl) phenyl] carbamoyl} amino) benzamide;
N- (2-methoxyethyl) -4-({[4- (4-morpholin-4-yl-6-piperidin-1-yl-1,3,5-triazin-2-yl) Phenyl] carbamoyl} amino) benzamide;
1- [4- (4-morpholin-4-yl-6-pyrrolidin-1-yl-1,3,5-triazin-2-yl) phenyl] -3- [4- (pyrrolidine -1-ylcarbonyl) phenyl] urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-ethylpiperazin-1-yl) carbonyl] phenyl} urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;
Methyl 4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} benzoate;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) urea;
1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -{4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;
1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- (4- {4-[(3S) -3-methylmorpholin-4-yl ] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;
4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) Carbamoyl] amino} benzoic acid;
1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6-mor Folin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;
N- [3- (dimethylamino) propyl] -4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3 , 5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) Carbamoyl] amino} -N- (2-pyrrolidin-1-ylethyl) benzamide;
1- (4- {4-[(3R) -3-methylmorpholin-4-yl] -6-[(3S) -3-methylmorpholin-4-yl] -1,3,5-triazine -2-yl} phenyl) -3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (dipropylamino) piperidin-1-yl] carbonyl} phenyl) urea;
1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4-[(3R) -3-methylmorpholin-4-yl] -6- [ (3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) urea;
4-{[(4- {4-[(3R) -3-methylmorpholin-4-yl] -6-[(3S) -3-methylmorpholin-4-yl] -1,3,5- Triazin-2-yl} phenyl) carbamoyl] amino} benzoic acid;
1- {4-[(4-butylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4-[(3R) -3-methylmorpholin-4-yl] -6- [ (3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) urea;
Methyl 4-{[(4- {4-[(3R) -3-methylmorpholin-4-yl] -6-[(3S) -3-methylmorpholin-4-yl] -1,3,5 -Triazin-2-yl} phenyl) carbamoyl] amino} benzoate;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-butylpiperazin-1-yl) carbonyl] phenyl} urea;
1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- (4- {4-[(3R) -3-methylmorpholin-4-yl ] -6-[(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (2-methylpropyl) piperazin-1-yl] carbonyl} phenyl) urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (1-methylpropyl) piperazin-1-yl] carbonyl} phenyl) urea;
4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- [2- (4-methylpiperazin-1-yl) ethyl] benzamide;
N- [2- (dimethylamino) ethyl] -4-{[(4- {4-[(3R) -3-methylmorpholin-4-yl] -6-[(3S) -3-methylmorpholine -4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- (2-pyrrolidin-1-ylethyl) benzamide;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-propylpiperidin-1-yl) carbonyl] phenyl} urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- [4- (pi Ferridin-1-ylcarbonyl) phenyl] urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-propylpiperazin-1-yl) carbonyl] phenyl} urea;
4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} -N- (2-methoxyethyl) benzamide;
1- {4- [4-morpholin-4-yl-6- (4-tricyclo [3.3.1.13,7] dec-1-ylpiperazin-1-yl) -1,3,5-triazine -2-yl] phenyl} -3-pyridin-4-ylurea;
Methyl 4-{[(4- {4- [4- (dimethylcarbamoyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} Phenyl) carbamoyl] amino} benzoate;
N, N-dimethyl-4- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazine-2- (1) piperazine-1-carboxamide;
N, N-dimethyl-4- (4- {4-[({4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} carbamoyl) amino] phenyl} -6-morpholine- 4-yl-1,3,5-triazin-2-yl) piperazin-1-carboxamide;
N, N-dimethyl-4- {4-morpholin-4-yl-6- [4-({[4- (pyridazin-4-ylcarbamoyl) phenyl] carbamoyl} amino) phenyl]- 1,3,5-triazin-2-yl} piperazine-1-carboxamide;
N, N-dimethyl-4- (4-morpholin-4-yl-6- {4-[({4-[(4-propylpiperidin-1-yl) carbonyl] phenyl} carbamoyl) Amino] phenyl} -1,3,5-triazin-2-yl) piperazine-1-carboxamide;
4-{[(4- {4- [4- (dimethylcarbamoyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} benzoic acid;
4- (4- {4-[({4-[(2-methoxyethyl) carbamoyl] phenyl} carbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5 -Triazin-2-yl) -N, N-dimethylpiperazin-1-carboxamide;
4- [4- (4-{[(4-{[2- (dimethylamino) ethyl] (methyl) carbamoyl} phenyl) carbamoyl] amino} phenyl) -6-morpholin-4-yl- 1,3,5-triazin-2-yl] -N, N-dimethylpiperazin-1-carboxamide;
4- (4- {4-[({4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} carbamoyl) amino] phenyl} -6-morpholin-4-yl-1, 3,5-triazin-2-yl) -N, N-dimethylpiperazin-1-carboxamide;
1- (4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -Pyridin-4-ylurea;
Methyl 4-{[(4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} benzoate;
4-{[(4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) Carbamoyl] amino} benzoic acid;
N- [3- (dimethylamino) propyl] -4-{[(4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3 , 5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
N- [2- (dimethylamino) ethyl] -4-{[(4- {4- [4- (ethylsulfonyl) piperazin-1-yl] -6-morpholin-4-yl-1,3 , 5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
4-{[(4- {4- [4- (1-methylethyl) -1,4-diazepane-1-yl] -6-morpholin-4-yl-1,3,5-triazine- 2-yl} phenyl) carbamoyl] amino} benzoic acid;
Methyl 4-{[(4- {4- [4- (acetylamino) piperidin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} benzoate;
1- (4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholin-4-yl-1,3,5-triazine-2- Il} phenyl) -3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;
N- [1- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) pi Ferridin-4-yl] acetamide;
4-{[(4- {4- [4- (acetylamino) piperidin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) Carbamoyl] amino} benzoic acid;
N- [2- (dimethylamino) ethyl] -4-{[(4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholine-4 -Yl-1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
N- {1-[(4-{[(4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholin-4-yl-1, 3,5-triazin-2-yl} phenyl) carbamoyl] amino} phenyl) carbonyl] piperidin-4-yl} acetamide;
1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4- [4- (1-methylethyl) -1,4-diazepane-1- Il] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;
1- (4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholin-4-yl-1,3,5-triazine-2- Il} phenyl) -3- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ (3S) -3-methylmorpholin-4-yl] carbonyl} phenyl) urea;
1- {4-[(4-butylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4- [4- (1-methylethyl) -1,4-diazepane-1- Il] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;
1- (4- {4-[(4-methylpiperazin-1-yl) amino] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3- Phenylurea;
1- (4- {4-[(1-methylpiperidin-4-yl) oxy] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3 -Pyridin-4-ylurea;
1- {4- [4-morpholin-4-yl-6- (piperidin-4-yloxy) -1,3,5-triazin-2-yl] phenyl} -3-pyridine-4- Ilurea;
Ethyl 4-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) oxy] Piperidine-1-carboxylate;
N-ethyl-4-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl ) Oxy] piperidine-1-carboxamide;
tert-butyl 4-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) Oxy] piperidine-1-carboxylate;
4-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) oxy] py Ferridine-1-sulfonamide;
1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-pyridin-4-ylurea;
1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-pyridin-3-ylurea;
1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3-phenylurea;
1- [4- (dimethylamino) phenyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;
1- (4-cyanophenyl) -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl-1 , 3,5-triazin-2-yl] phenyl} urea;
1- {4- [4- (1,4-dioxa-8-azaspiro [4.5] deck-8-yl) -6-morpholin-4-yl-1,3,5-triazine-2- Il] phenyl} -3- (2-methylpyridin-4-yl) urea;
1- [2- (dimethylamino) ethyl] -3- {4- [4- (1,4-dioxa-8-azaspiro [4.5] dec-8-yl) -6-morpholin-4-yl -1,3,5-triazin-2-yl] phenyl} urea;
1- [4- (4-morpholin-4-yl-6-quinolin-3-yl-1,3,5-triazin-2-yl) phenyl] -3-pyridin-4-ylurea;
1- {4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea ;
Methyl 4-[({4- [4- (2-methoxyethoxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} carbamoyl) amino] Benzoate;
1- (4- {4-morpholin-4-yl-6- [2- (pyridin-4-ylamino) ethyl] -1,3,5-triazin-2-yl} phenyl) -3-pyridine -4-ylurea;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) -N-methylbenzamide;
N- [2- (dimethylamino) ethyl] -4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carr Barmoyl} amino) benzamide;
4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N-methyl-N- [2- (methylamino) ethyl] benzamide;
1- [4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- {4-[(4-methylpiperazin-1 -Yl) carbonyl] phenyl} urea;
1- {4-[(3,3-dimethylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (4-methoxy-6-morpholin-4-yl-1,3,5 -Triazin-2-yl) phenyl] urea;
4-({[4- (4-methoxy-6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] carbamoyl} amino) -N- (2-py Ferridin-1-ylethyl) benzamide;
1- (4- {4- [2,5-bis (hydroxymethyl) pyrrolidin-1-yl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} Phenyl) -3-pyridin-4-ylurea;
1- (4- {4- [2- (1,3-dioxan-2-yl) ethyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-ylurea;
1- (4- {4- [3- (dimethylamino) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) -3-pyridin-4-yl Urea;
1- [4- (4- {3-[(1-methylethyl) amino] propyl} -6-morpholin-4-yl-1,3,5-triazin-2-yl) phenyl] -3- Pyridin-4-ylurea;
1- {4- [4-morpholin-4-yl-6- (3-pyrrolidin-1-ylpropyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridine- 4-ylurea;
1- (4- {4- [3- (4-methylpiperazin-1-yl) propyl] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl)- 3-pyridin-4-ylurea;
1- {4- [4- (3-{[2- (dimethylamino) ethyl] amino} propyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
1- {4- [4- (3-hydroxypropyl) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
1- {4- [4-morpholin-4-yl-6- (3-oxopropyl) -1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-ylurea;
N- (4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-triazin-2-yl) benzenesulfonamide;
N- {4- [4-({[4- (4-methylpiperazin-1-yl) phenyl] carbamoyl} amino) phenyl] -6-morpholin-4-yl-1,3,5- Triazin-2-yl} benzenesulfonamide;
N- (4- {4-[({4- [2- (dimethylamino) ethoxy] phenyl} carbamoyl) amino] phenyl} -6-morpholin-4-yl-1,3,5-tri Azin-2-yl) benzenesulfonamide;
N- (4- {4-[({4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} carbamoyl) amino] phenyl} -6-morpholin-4-yl-1, 3,5-triazin-2-yl) benzenesulfonamide;
N- {4-morpholin-4-yl-6- [4-({[4- (piperazin-1-ylcarbonyl) phenyl] carbamoyl} amino) phenyl] -1,3,5-tri Azin-2-yl} benzenesulfonamide;
N- [4- (4-{[(4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) carbamoyl] amino} phenyl) -6-morpholine-4- Yl-1,3,5-triazin-2-yl] benzenesulfonamide;
N- [2- (dimethylamino) ethyl] -N-methyl-4-{[(4- {4-morpholin-4-yl-6-[(phenylsulfonyl) amino] -1,3,5- Triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
N- [2- (dimethylamino) ethyl] -4-{[(4- {4-morpholin-4-yl-6-[(phenylsulfonyl) amino] -1,3,5-triazine-2 -Yl} phenyl) carbamoyl] amino} benzamide;
Methyl 4-{[(4- {4-morpholin-4-yl-6-[(phenylsulfonyl) amino] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} Benzoate;
4-{[(4- {4-morpholin-4-yl-6-[(phenylsulfonyl) amino] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzoic acid ;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- [4- (6-morpholin-4-yl-4-oxo-4,5-dihydro-1 , 3,5-triazin-2-yl) phenyl] urea;
1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) Phenyl) urea;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropyl-2-methylpiperazin-1- Carbonyl) phenyl) urea;
1- (4- (4-cyclobutyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazine-2 -Yl) phenyl) urea;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropyl-3-methylpiperazin-1- Carbonyl) phenyl) urea;
1- (4- (3,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) Phenyl) urea;
1- (4- (4-cyclobutyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazine-2 -Yl) phenyl) urea;
1- (4- (4-cyclobutylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl Urea;
1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-isopropyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl ) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-cyclobutyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl ) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-isopropyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl ) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (3,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-cyclobutyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl ) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-cyclobutylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1, 3,5-triazin-2-yl) phenyl) urea;
1- (4- (2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1,3 , 5-triazin-2-yl) phenyl) urea;
1- (4- (3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1,3 , 5-triazin-2-yl) phenyl) urea;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3-methylpiperazin-1-carbonyl) phenyl) Urea;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (2-methylpiperazin-1-carbonyl) phenyl) Urea;
1- (4- (3,3-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) Phenyl) urea;
1- (4- (3,3-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) -3- (4- (3 , 3,4-trimethylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4,6-dimorpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3,3,4-trimethylpiperazin-1-car Carbonyl) phenyl) urea;
1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-isopropyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-cyclobutyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-isopropyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (3,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4 -Yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-cyclobutyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H- Pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-cyclobutylpiperazine-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4- Yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) -3- (4- (3,3,4-trimethylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (3,3-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4 -Yl) -1,3,5-triazin-2-yl) phenyl) urea;
N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) ureido) benzamide;
N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3 , 5-triazin-2-yl) phenyl) ureido) benzamide;
1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran -4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5 -Triazin-2-yl) phenyl) urea;
1- (4- (2,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5 -Triazin-2-yl) phenyl) urea;
1- (4- (4-isopropyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1, 3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-cyclobutyl-2-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1, 3,5-triazin-2-yl) phenyl) urea;
N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5-triazine -2-yl) phenyl) ureido) benzamide;
1- (4- (4-isopropyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1, 3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3-methylpiperazin -1-carbonyl) phenyl) urea;
1- (4- (3,4-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5 -Triazin-2-yl) phenyl) urea;
1- (4- (4-cyclobutyl-3-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1, 3,5-triazin-2-yl) phenyl) urea;
1- (4- (3,3-dimethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5 -Triazin-2-yl) phenyl) urea;
1- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3,3,4 -Trimethylpiperazine-1-carbonyl) phenyl) urea;
1- (4- (4-cyclobutylpiperazine-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5- Triazin-2-yl) phenyl) urea;
N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3,5-triazin-2-yl ) Phenyl) ureido) benzamide;
1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3 , 5-triazin-2-yl) phenyl) urea;
1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (2-methylmorpholino) -6-morpholino-1,3 , 5-triazin-2-yl) phenyl) urea;
1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran -4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea;
1- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl ) -6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (quinucridin-4-yl) phenyl) urea;
1- (4- (4-cyclopropylpiperazin-1-yl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6 -((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (cyclopropylmethyl) piperazin-1-yl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl ) -6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-yl) phenyl) urea;
1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-yl) phenyl) urea;
1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazine-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidine-1- Yl) -6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1,3,5- Triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-cyclopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidin-1-yl)- 6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (cyclopropylmethyl) piperazin-1-carbonyl) phenyl) -3- (4- (4-((2R, 5S) -2,5-dimethylpyrrolidine-1- Yl) -6-((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-yl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethylamino) piperidin-1-yl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (quinucridin-4-yl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-cyclopropylpiperazin-1-yl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4- (cyclopropylmethyl) piperazin-1-yl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-yl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-yl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4-cyclopropylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-((2S, 5R) -2,5-bis (hydroxymethyl) pyrrolidin-1-yl) -6-((R) -3-methylmorpholino) -1 , 3,5-triazin-2-yl) phenyl) -3- (4- (4- (cyclopropylmethyl) piperazin-1-carbonyl) phenyl) urea;
1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) Urea;
1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-3-yl) Urea;
1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (pyridazin-4-yl Urea;
1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (pyrimidin-5-yl Urea;
4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) ureido) benzamide;
N- (2- (dimethylamino) ethyl) -4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazine-2 -Yl) phenyl) ureido) benzamide;
N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5- Triazin-2-yl) phenyl) ureido) benzamide;
N- (2- (methylamino) ethyl) -4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazine-2 -Yl) phenyl) ureido) benzamide;
N-methyl-N- (2- (methylamino) ethyl) -4- (3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5- Triazin-2-yl) phenyl) ureido) benzamide;
1- (4-((R) -3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydrofuran-3-yljade C) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl) -3- (4- (piperazin- 1-carbonyl) phenyl) urea;
1- (4- (4-methylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5 -Triazin-2-yl) phenyl) urea;
1- (4- (4-ethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3,5 -Triazin-2-yl) phenyl) urea;
1- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4-morpholino-6- (tetrahydrofuran-3-yloxy) -1,3, 5-triazin-2-yl) phenyl) urea;
1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (pyridin-4-yl) urea;
1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (pyridin-3-yl) urea;
1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (pyridazin-4-yl) urea;
1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (pyrimidin-5-yl) urea;
4- (3- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) Phenyl) ureido) benzamide;
1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydro Furan-3-yloxy) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (4- (piperazin-1-carbonyl) phenyl) urea;
1- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3-yloxy) -1,3,5-triazin-2-yl) phenyl)- 3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-ethylpiperazin-1-carbonyl) phenyl) -3- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3- Yloxy) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4-((S) -3-methylmorpholino) -6- (tetrahydrofuran-3 -Yloxy) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine-3- Urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridazine-4 -Yl) urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyrimidine-5 -Yl) urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine-4- Urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenylurea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4-chlorophenyl Urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4-fluoro Phenyl) urea;
Methyl 4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzo Eight;
4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzoic acid;
4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N -(2- (dimethylamino) ethyl) benzamide;
4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) -N -(2- (dimethylamino) ethyl) -N-methylbenzamide;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (3 -(Dimethylamino) pyrrolidine-1-carbonyl) phenyl) urea;
4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzamide ;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (pipe Razin-1-carbonyl) phenyl) urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4 Ethylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4 Isopropylpiperazine-1-carbonyl) phenyl) urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4 -(Dimethylamino) piperidine-1-carbonyl) phenyl) urea;
1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (4-methyl-1,4-diazepan-1-yl) -6 Morpholino-1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (piperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-n-propylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (4-methyl-1,4-diazepan-1-yl) -6 Morpholino-1,3,5-triazin-2-yl) phenyl) urea;
N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (4-methyl-1,4-diazepan-1-yl) -6-morpholino-1,3, 5-triazin-2-yl) phenyl) ureido) benzamide;
N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (4-methyl-1,4-diazepan-1-yl) -6-morpholino- 1,3,5-triazin-2-yl) phenyl) ureido) benzamide;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenyl Urea;
1- (4-chlorophenyl) -3- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine-2 -Yl) phenyl) urea;
1- (4-fluorophenyl) -3- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine- 2-yl) phenyl) urea;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-3-yl) urea;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-4-yl) urea;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridazin-4-yl) urea;
1- (4- (4- (4-methyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyrimidin-5-yl) urea;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (piperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-n-propylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (4-ethyl-1,4-diazepan-1-yl) -6 Morpholino-1,3,5-triazin-2-yl) phenyl) urea;
N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (4-ethyl-1,4-diazepan-1-yl) -6-morpholino-1,3, 5-triazin-2-yl) phenyl) ureido) benzamide;
N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (4-ethyl-1,4-diazepan-1-yl) -6-morpholino- 1,3,5-triazin-2-yl) phenyl) ureido) benzamide;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenyl Urea;
1- (4-chlorophenyl) -3- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine-2 -Yl) phenyl) urea;
1- (4-fluorophenyl) -3- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine- 2-yl) phenyl) urea;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-3-yl) urea;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-4-yl) urea;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridazin-4-yl) urea;
1- (4- (4- (4-ethyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyrimidin-5-yl) urea;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (piperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-n-propylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (4-propyl-1,4-diazepan-1-yl) -6 Morpholino-1,3,5-triazin-2-yl) phenyl) urea;
N- (2- (dimethylamino) ethyl) -4- (3- (4- (4- (4-propyl-1,4-diazepan-1-yl) -6-morpholino-1,3, 5-triazin-2-yl) phenyl) ureido) benzamide;
N- (2- (dimethylamino) ethyl) -N-methyl-4- (3- (4- (4- (4-propyl-1,4-diazepan-1-yl) -6-morpholino- 1,3,5-triazin-2-yl) phenyl) ureido) benzamide;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenyl Urea;
1- (4-chlorophenyl) -3- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine-2 -Yl) phenyl) urea;
1- (4-fluorophenyl) -3- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazine- 2-yl) phenyl) urea;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-3-yl) urea;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-4-yl) urea;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridazin-4-yl) urea;
1- (4- (4- (4-propyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyrimidin-5-yl) urea;
1- (4- (4- (4-isopropyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (Pyridin-3-yl) urea;
1- (4- (4- (4-isopropyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (Pyridin-4-yl) urea;
1- (4- (4- (4-isopropyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (Pyridazin-4-yl) urea;
1- (4- (4- (4-isopropyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (Pyrimidin-5-yl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-3-yl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridin-4-yl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyridazin-4-yl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( Pyrimidin-5-yl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenyl Urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4-chlorophenyl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4-fluorophenyl) urea;
Methyl-4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl ) Ureido) benzoate;
4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urei Benzoic acid;
4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urei Fig.)-N- (2- (dimethylamino) ethyl) benzamide;
4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urei Fig.)-N- (2- (dimethylamino) ethyl) -N-methylbenzamide;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) urea;
4- (3- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urei Benzamide;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-ethylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-n-propylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (piperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-acetyl-1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- ( 4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) urea;
1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(4- (piperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-ethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-mor Polyno-1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(4- (4-isopropylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -Phenylurea;
1- (4-chlorophenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazine -2-yl) phenyl) urea;
1- (4-fluorophenyl) -3- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-tri Azin-2-yl) phenyl) urea;
1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(Pyridin-4-yl) urea;
1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(Pyridazin-4-yl) urea;
1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(Pyridin-3-yl) urea;
1- (4- (4- (4-isobutyryl-1,4-diazepan-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3 -(Pyrimidin-5-yl) urea;
tert-butyl 4- (4- (4- (3- (4- (methoxycarbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazin-2-yl) -1,4-diazepan-1-carboxylate;
Methyl 4- (3- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) benzo Eight;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenylurea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4-chlorophenyl Urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4-fluoro Phenyl) urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine-3- Urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine-4- Urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridazine-4 -Yl) urea;
1- (4- (4- (1,4-diazepane-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyrimidine-5 -Yl) urea;
N-methyl-4- (4-morpholino-6- (4- (3-phenylureido) phenyl) -1,3,5-triazin-2-yl) -1,4-diazepane-1 -Carboxamide (M + H) 532.2;
4- (4- (4- (3- (4-chlorophenyl) ureido) phenyl) -6-morpholino-1,3,5-triazin-2-yl) -N-methyl-1,4 Diazephan-1-carboxamide;
4- (4- (4- (3- (4-fluorophenyl) ureido) phenyl) -6-morpholino-1,3,5-triazin-2-yl) -N-methyl-1, 4-diazepan-1-carboxamide;
4- (4- (4- (3- (4- (2- (dimethylamino) ethylcarbamoyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazine-2 -Yl) -N-methyl-1,4-diazepane-1-carboxamide;
4- (4- (4- (3- (4-((2- (dimethylamino) ethyl) (methyl) carbamoyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5 -Triazin-2-yl) -N-methyl-1,4-diazepane-1-carboxamide;
4- (4- (4- (3- (4-carbamoylphenyl) ureido) phenyl) -6-morpholino-1,3,5-triazin-2-yl) -N-methyl-1 , 4-diazepan-1-carboxamide;
4- (4- (4- (3- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5- Triazin-2-yl) -N-methyl-1,4-diazepane-1-carboxamide;
N-methyl-4- (4-morpholino-6- (4- (3- (4- (piperazin-1-carbonyl) phenyl) ureido) phenyl) -1,3,5-triazine- 2-yl) -1,4-diazepane-1-carboxamide;
N-methyl-4- (4- (4- (3- (4- (4-methylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5- Triazin-2-yl) -1,4-diazepane-1-carboxamide;
4- (4- (4- (3- (4- (4-ethylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazine-2 -Yl) -N-methyl-1,4-diazepane-1-carboxamide;
4- (4- (4- (3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazine- 2-yl) -N-methyl-1,4-diazepane-1-carboxamide;
4- (4- (4- (3- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5- Triazin-2-yl) -N-methyl-1,4-diazepane-1-carboxamide;
4- (4- (4- (3- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5- Triazin-2-yl) -N-isopropyl-1,4-diazepane-1-carboxamide;
N-isopropyl-4- (4- (4- (3- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3, 5-triazin-2-yl) -1,4-diazepane-1-carboxamide;
4- (4- (4- (3- (4- (4-ethylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5-triazine-2 -Yl) -N-isopropyl-1,4-diazepane-1-carboxamide;
N-isopropyl-4- (4- (4- (3- (4- (4-methylpiperazin-1-carbonyl) phenyl) ureido) phenyl) -6-morpholino-1,3,5 -Triazin-2-yl) -1,4-diazepane-1-carboxamide;
N-isopropyl-4- (4-morpholino-6- (4- (3- (4- (piperazin-1-carbonyl) phenyl) ureido) phenyl) -1,3,5-triazine -2-yl) -1,4-diazepane-1-carboxamide;
N-isopropyl-4- (4-morpholino-6- (4- (3-pyridin-4-ylureido) phenyl) -1,3,5-triazin-2-yl) -1,4 Diazephan-1-carboxamide;
N-isopropyl-4- (4-morpholino-6- (4- (3-pyridazin-4-ylureido) phenyl) -1,3,5-triazin-2-yl) -1, 4-diazepan-1-carboxamide;
N-isopropyl-4- (4-morpholino-6- (4- (3-pyrimidin-5-ylureido) phenyl) -1,3,5-triazin-2-yl) -1, 4-diazepan-1-carboxamide;
N-isopropyl-4- (4-morpholino-6- (4- (3-pyridin-3-ylureido) phenyl) -1,3,5-triazin-2-yl) -1,4 Diazephan-1-carboxamide;
1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-3-yl) Urea;
1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridin-4-yl) Urea;
1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyridazin-4-yl Urea;
1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3- (pyrimidin-5-yl Urea;
1- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) -3-phenylurea;
1- (4-chlorophenyl) -3- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) urea ;
1- (4-fluorophenyl) -3- (4- (4-morpholino-6- (1H-pyrazol-1-yl) -1,3,5-triazin-2-yl) phenyl) Urea;
1- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenylurea;
1- (4-chlorophenyl) -3- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl ) Phenyl) urea;
1- (4-fluorophenyl) -3- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazine-2- Yl) phenyl) urea;
1- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine- 4-yl) urea;
1- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridazine -4-yl) urea;
1- (4- (4- (2-methyl-1H-imidazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyrimidine -5-yl) urea;
1- (4-acetylphenyl) -3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (piperazin-1 -Yl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2- (dimethyl Amino) acetyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-morpholi Noacetyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-hydroxy Acetyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (methoxymethyl) Phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-methoxy Ethyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (1-hydroxy Ethyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-hydroxy Propan-2-yl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-hydroxy Propyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (2-hydroxy -2-methylpropyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4- (4- (dimethyl Amino) piperidine-1-carbonyl) phenyl) urea;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (4-cyanophenyl) urea ;
4- (3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) ureido) -N-methylbenz amides;
4- (3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) ureido) -N, N- Dimethylbenzamide;
4- (3- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) ureido) benzamide;
1- (4- (4,6-bis ((R) -3-methylmorpholino) -1,3,5-triazin-2-yl) phenyl) -3- (6- (4-methylpipepe Razin-1-carbonyl) pyridin-3-yl) urea;
(R) -1- (4-((dimethylamino) methyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (pyridin-4-yl) urea;
(R) -1- (4-acetylphenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5 -Triazin-2-yl) phenyl) urea;
(R) -1- (4- (2- (dimethylamino) acetyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4- Yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (4- (2-morpholinoacetyl) phenyl) urea;
(R) -1- (4- (2-hydroxyacetyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (methoxymethyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1 , 3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (2-methoxyethyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (1-hydroxyethyl) phenyl) -3- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (2-hydroxypropan-2-yl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran- 4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (2-hydroxypropyl) phenyl) -3- (4- (4-((R) -3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (2-hydroxy-2-methylpropyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran- 4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro -2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl) urea;
(R) -1- (4-cyanophenyl) -3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3, 5-triazin-2-yl) phenyl) urea;
(R) -N-methyl-4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-tri Azin-2-yl) phenyl) ureido) benzamide;
(R) -N, N-dimethyl-4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5 -Triazin-2-yl) phenyl) ureido) benzamide;
(R) -4- (3- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazine-2- Yl) phenyl) ureido) benzamide;
(R) -1- (4- (4- (3-methylmorpholino) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl) phenyl ) -3- (6- (4-methylpiperazin-1-carbonyl) pyridin-3-yl) urea;
1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyrimidine -5-yl) urea;
1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine- 3-yl) urea;
1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridine- 4-yl) urea;
1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (pyridazine -4-yl) urea;
1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3-phenylurea;
1- (4-chlorophenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl ) Phenyl) urea;
1- (4-fluorophenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazine-2- Yl) phenyl) urea;
Methyl 4- (3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido ) Benzoate;
4- (3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) Benzoic acid;
4- (3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) ureido) Benzamide;
1- (4- (3- (dimethylamino) pyrrolidine-1-carbonyl) phenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-mor Polyno-1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (Piperazin-1-carbonyl) phenyl) urea;
1- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1,3,5-triazin-2-yl) phenyl) -3- (4- (4-methylpiperazin-1-carbonyl) phenyl) urea;
1- (4- (4-ethylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino-1 , 3,5-triazin-2-yl) phenyl) urea;
1- (4- (4-isopropylpiperazin-1-carbonyl) phenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-morpholino- 1,3,5-triazin-2-yl) phenyl) urea;
1- (4- (4- (dimethylamino) piperidine-1-carbonyl) phenyl) -3- (4- (4- (3-methyl-1H-pyrazol-1-yl) -6-mor Polyno-1,3,5-triazin-2-yl) phenyl) urea;
1- {4-[(4-butylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4- [4- (1-methylethyl) -1,4-diazepane-1- Il] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;
1- (4- {4- [4- (1-methylethyl) -1,4-diazepan-1-yl] -6-morpholin-4-yl-1,3,5-triazine-2- Il} phenyl) -3- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) urea;
1- {4-[(4-ethylpiperazin-1-yl) carbonyl] phenyl} -3- (4- {4- [4- (1-methylethyl) -1,4-diazepane-1- Il] -6-morpholin-4-yl-1,3,5-triazin-2-yl} phenyl) urea;
1- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4- Yl) -1,3,5-triazin-2-yl] phenyl} urea;
1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;
1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl-1 , 3,5-triazin-2-yl) phenyl] urea;
1- (4-{[4- (1-methylethyl) piperazin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetrahydro-2H -Pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;
N- [2- (dimethylamino) ethyl] -N-methyl-4-[({4- [4-morpholin-4-yl-6- (tetrahydro-2H-pyran-4-yl) -1, 3,5-triazin-2-yl] phenyl} carbamoyl) amino] benzamide;
1- {4- [4- (azetidin-3-yloxy) -6-morpholin-4-yl-1,3,5-triazin-2-yl] phenyl} -3-pyridin-4-yl Urea;
N- (1-methylethyl) -3-[(4-morpholin-4-yl-6- {4-[(pyridin-4-ylcarbamoyl) amino] phenyl} -1,3,5-tri Azin-2-yl) oxy] azetidine-1-carboxamide;
N- {1-[(4-{[(4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl ) Carbamoyl] amino} phenyl) carbonyl] piperidin-4-yl} acetamide;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ 4- (1-methylethyl) -1,4-diazepan-1-yl] carbonyl} phenyl) urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- [4- (3 Oxa-8-azabicyclo [3.2.1] oct-8-ylcarbonyl) phenyl] urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- {4-[( 4-cyanopiperidin-1-yl) carbonyl] phenyl} urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ (3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) urea;
1- (4- {4,6-bis [(3S) -3-methylmorpholin-4-yl] -1,3,5-triazin-2-yl} phenyl) -3- (4-{[ (3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) urea;
1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;
1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;
1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- {4-[(2-methylpiperazin-1 -Yl) carbonyl] phenyl} urea;
1- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazine -2-yl} phenyl) -3- [4- (piperazin-1-ylcarbonyl) phenyl] urea;
1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;
1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- {4-[(3,3,4-trimethyl Piperazin-1-yl) carbonyl] phenyl} urea;
1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- (4-{[(3R) -3-methyl Piperazin-1-yl] carbonyl} phenyl) urea;
1- (4-{[(3R) -3,4-dimethylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4,6-di (morpholin-4-yl) -1 , 3,5-triazin-2-yl] phenyl} urea;
1- (4-{[(3R) -4-cyclobutyl-3-methylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4,6-di (morpholin-4-yl ) -1,3,5-triazin-2-yl] phenyl} urea;
1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- (4-{[(3R) -3-methyl -4- (propan-2-yl) piperazin-1-yl] carbonyl} phenyl) urea;
1- {4- [4,6-di (morpholin-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- (4-{[(3S) -3-methyl Piperazin-1-yl] carbonyl} phenyl) urea;
N- [2- (dimethylamino) ethyl] -N-methyl-4-{[(4- {4-[(3S) -3-methylmorpholin-4-yl] -6- [4- (propane- 2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
1- (4- {4-[(3S) -3-methylmorpholin-4-yl] -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1 , 3,5-triazin-2-yl} phenyl) -3- {4-[(4-methylpiperazin-1-yl) carbonyl] phenyl} urea;
1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- (4- {4-[(3S) -3-methylmorpholine- 4-yl] -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;
N- [3- (dimethylamino) propyl] -4-{[(4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepane -1-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
N- [2- (dimethylamino) ethyl] -N-methyl-4-{[(4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1, 4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
1- [4- (morpholin-4-ylcarbonyl) phenyl] -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1, 4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;
N- (2-methoxyethyl) -4-{[(4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepane-1 -Yl] -1,3,5-triazin-2-yl} phenyl) carbamoyl] amino} benzamide;
1- [4- (1,4-diazepane-1-ylcarbonyl) phenyl] -3- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl ) -1,4-diazepan-1-yl] -1,3,5-triazin-2-yl} phenyl) urea;
1- (4- {4- (morpholin-4-yl) -6- [4- (propan-2-yl) -1,4-diazepan-1-yl] -1,3,5-triazine -2-yl} phenyl) -3- (4-{[4- (propan-2-yl) -1,4-diazepan-1-yl] carbonyl} phenyl) urea;
1- (4-{[(3S) -4-cyclobutyl-3-methylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4,6-di (morpholin-4-yl ) -1,3,5-triazin-2-yl] phenyl} urea;
1- (4-{[(3S) -3,4-dimethylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4,6-di (morpholin-4-yl) -1 , 3,5-triazin-2-yl] phenyl} urea;
1- {4- [4- (morpholin-4-yl) -6- (tetrahydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} -3- {4-[(3,3,4-trimethylpiperazin-1-yl) carbonyl] phenyl} urea;
1- (4-{[(3S) -3,4-dimethylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4- (morpholin-4-yl) -6- (tetra Hydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;
1- (4-{[(3S) -3-methylpiperazin-1-yl] carbonyl} phenyl) -3- {4- [4- (morpholin-4-yl) -6- (tetrahydro- 2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea;
1- (4-{[(3R) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetra Hydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea; And
1- (4-{[(3S) -3- (dimethylamino) pyrrolidin-1-yl] carbonyl} phenyl) -3- {4- [4-morpholin-4-yl-6- (tetra Hydro-2H-pyran-4-yl) -1,3,5-triazin-2-yl] phenyl} urea
&Lt; / RTI &gt; or a pharmaceutically acceptable salt thereof. 제12항에 있어서, 1-(4-{[4-(디메틸아미노)피페리딘-1-일]카르보닐}페닐)-3-[4-(4,6-디모르폴린-4-일-1,3,5-트리아진-2-일)페닐]우레아인 화합물 또는 그의 제약상 허용되는 염.13. A compound according to claim 12, wherein 1- (4-{[4- (dimethylamino) piperidin-1-yl] carbonyl} phenyl) -3- [4- (4,6-dimorpholin-4-yl -1,3,5-triazin-2-yl) phenyl] ureain compound or a pharmaceutically acceptable salt thereof. 제1항의 화합물 및 제약상 허용되는 담체를 포함하는, 재협착, 아테롬성동맥경화증, 골 장애, 관절염, 당뇨병성 망막병증, 건선, 양성 전립선 비대증, 아테롬성동맥경화증, 염증, 혈관신생, 면역 장애, 췌장염, 신장 질환 및 암으로부터 선택되는 PI3K(phosphatidylinositol-3 kinase; 포스파티딜이노시톨-3 키나제)-관련 장애, mTOR(mammalian target of rapamycin; 라파마이신 포유동물 표적)-관련 장애 또는 hSMG-1(human serine/threonine-protein kinase; 인간 세린/트레오닌-단백질 키나제)-관련 장애의 치료가 필요한 포유동물에서 이를 치료하기 위한 제약 조성물.Restenosis, atherosclerosis, bone disorders, arthritis, diabetic retinopathy, psoriasis, benign prostatic hyperplasia, atherosclerosis, inflammation, angiogenesis, immune disorders, pancreatitis, comprising the compound of claim 1 and a pharmaceutically acceptable carrier Phosphatidylinositol-3 kinase (phosphatidylinositol-3 kinase) -related disorders selected from renal disease and cancer, mammalian target of rapamycin (rapamycin mammalian target) -related disorders or hSMG-1 (human serine / threonine) A pharmaceutical composition for treating a protein kinase in a mammal in need of treatment of a human serine / threonine-protein kinase-related disorder. 제14항에 있어서, 경구 투여 및 조성물에 적합한 제약상 허용되는 담체가 경구 투여 형태를 포함하는 것인 제약 조성물.The pharmaceutical composition of claim 14, wherein the pharmaceutically acceptable carrier suitable for oral administration and composition comprises an oral dosage form. 제1항의 화합물; 토포이소머라제 I 억제제, MEK(mitogen-activated protein extracellular-signal-regulated kinase; 미토겐-활성화 단백질 세포외-신호-조절 키나제) 1/2 억제제, HSP90(heat shock protein 90; 열 충격 단백질 90) 억제제, 프로카르바진, 다카르바진, 겜시타빈, 카페시타빈, 메토트렉세이트, 탁솔, 탁소테레, 머캅토퓨린, 티오구아닌, 히드록시우레아, 시타라빈, 시클로포스파미드, 이포스파미드, 니트로소우레아, 시스플라틴, 카르보플라틴, 미토마이신, 다카르바진, 프로카르비진, 에토포시드, 테니포시드, 캄파테신, 블레오마이신, 독소루비신, 이다루비신, 다우노루비신, 닥티노마이신, 플리카마이신, 미톡산트론, L-아스파라기나제, 독소루비신, 에피루비신, 5-플루오로우라실, 도세탁셀, 파클리탁셀, 류코보린, 레바미솔, 이리노테칸, 에스트라무스틴, 에토포시드, 질소 머스타드, BCNU(bis-chloroethyl nitrosourea; 비스-클로로에틸 니트로소우레아), 카르무스틴, 로무스틴, 빈블라스틴, 빈크리스틴, 비노렐빈, 시스플라틴, 카르보플라틴, 옥살리플라틴, 이마티닙 메실레이트, 아바스틴 (베바시주맙), 헥사메틸멜라민, 토포테칸, 티로신 키나제 억제제, 티르포스틴, 헤르비마이신 A, 제니스테인, 에르브스타틴, 히드록시진, 글라티라머 아세테이트, 인터페론 베타-1a, 인터페론 베타-1b, 나탈리주맙 및 라벤두스틴 A로 이루어진 군으로부터 선택된 제2 화합물; 및 제약상 허용되는 담체를 포함하는,
재협착, 아테롬성동맥경화증, 골 장애, 관절염, 당뇨병성 망막병증, 건선, 양성 전립선 비대증, 아테롬성동맥경화증, 염증, 혈관신생, 면역 장애, 췌장염, 신장 질환 및 암으로부터 선택되는 PI3K(phosphatidylinositol-3 kinase; 포스파티딜이노시톨-3 키나제)-관련 장애, mTOR(mammalian target of rapamycin; 라파마이신 포유동물 표적)-관련 장애 또는 hSMG-1(human serine/threonine-protein kinase; 인간 세린/트레오닌-단백질 키나제)-관련 장애의 치료가 필요한 포유동물에서 이를 치료하기 위한 제약 조성물. A compound of claim 1; Topoisomerase I inhibitor, mitogen-activated protein extracellular-signal-regulated kinase (MEK) 1/2 inhibitor, heat shock protein 90 (HSP90) Inhibitors, procarbazine, dacarbazine, gemcitabine, capecitabine, methotrexate, taxol, taxotere, mercaptopurine, thioguanine, hydroxyurea, cytarabine, cyclophosphamide, ifosfamide, nitrosourea, Cisplatin, carboplatin, mitomycin, dacarbazine, procarbazine, etoposide, teniposide, camppatin, bleomycin, doxorubicin, idarubicin, daunorubicin, dactinomycin, plicamycin, mitoxane Tron, L-asparaginase, doxorubicin, epirubicin, 5-fluorouracil, docetaxel, paclitaxel, leucovorin, levamisol, irinotecan, esturamustine, etoposide, nitrogen mustard, BCNU (bi s-chloroethyl nitrosourea; bis-chloroethyl nitrosourea), carmustine, lomustine, vinblastine, vincristine, vinorelbine, cisplatin, carboplatin, oxaliplatin, imatinib mesylate, avastin (bevacizumab), Hexamethylmelamine, topotecan, tyrosine kinase inhibitors, tyrphostin, herbimycin A, genistein, ervstatin, hydroxyzine, glatiramer acetate, interferon beta-1a, interferon beta-1b, natalizumab, and rabendu A second compound selected from the group consisting of Stine A; And a pharmaceutically acceptable carrier,
PI3K (phosphatidylinositol-3 kinase) selected from restenosis, atherosclerosis, bone disorders, arthritis, diabetic retinopathy, psoriasis, benign prostatic hyperplasia, atherosclerosis, inflammation, angiogenesis, immune disorders, pancreatitis, kidney disease and cancer Phosphatidylinositol-3 kinase) -related disorders, mammalian target of rapamycin (rapamycin mammalian target) -related disorders or hSMG-1 (human serine / threonine-protein kinase) -related disorders Pharmaceutical compositions for treating them in a mammal in need thereof. 제16항에 있어서, 제2 화합물이 아바스틴인 제약 조성물.The pharmaceutical composition of claim 16, wherein the second compound is Avastin. 삭제delete 삭제delete 제14항 또는 제16항에 있어서, PI3K-관련 장애, mTOR-관련 장애 또는 hSMG-1-관련 장애가 암인 제약 조성물.The pharmaceutical composition of claim 14 or 16, wherein the PI3K-related disorder, mTOR-related disorder or hSMG-1-related disorder is cancer. 제20항에 있어서, 암이 백혈병, 피부암, 방광암, 유방암, 자궁암, 난소암, 전립선암, 폐암, 결장암, 췌장암, 신장암, 위암 및 뇌암으로 이루어진 군으로부터 선택된 것인 제약 조성물.The pharmaceutical composition of claim 20, wherein the cancer is selected from the group consisting of leukemia, skin cancer, bladder cancer, breast cancer, uterine cancer, ovarian cancer, prostate cancer, lung cancer, colon cancer, pancreatic cancer, kidney cancer, gastric cancer and brain cancer. 제1항의 화합물 및 제약상 허용되는 담체를 포함하는, 진행성 신세포 암종, 급성 림프모구성 백혈병, 급성 악성 흑색종, 또는 연조직 또는 골 육종의 치료가 필요한 포유동물에서 상기 진행성 신세포 암종, 급성 림프모구성 백혈병, 급성 악성 흑색종, 또는 연조직 또는 골 육종을 치료하기 위한 제약 조성물. The advanced renal cell carcinoma, acute lymph, in a mammal in need of treatment of advanced renal cell carcinoma, acute lymphoblastic leukemia, acute malignant melanoma, or soft tissue or bone sarcoma, comprising the compound of claim 1 and a pharmaceutically acceptable carrier. Pharmaceutical compositions for the treatment of parental leukemia, acute malignant melanoma, or soft tissue or bone sarcoma. 제1항의 화합물; 토포이소머라제 I 억제제, MEK(mitogen-activated protein extracellular-signal-regulated kinase; 미토겐-활성화 단백질 세포외-신호-조절 키나제) 1/2 억제제, HSP90(heat shock protein 90; 열 충격 단백질 90) 억제제, 프로카르바진, 다카르바진, 겜시타빈, 카페시타빈, 메토트렉세이트, 탁솔, 탁소테레, 머캅토퓨린, 티오구아닌, 히드록시우레아, 시타라빈, 시클로포스파미드, 이포스파미드, 니트로소우레아, 시스플라틴, 카르보플라틴, 미토마이신, 다카르바진, 프로카르비진, 에토포시드, 테니포시드, 캄파테신, 블레오마이신, 독소루비신, 이다루비신, 다우노루비신, 닥티노마이신, 플리카마이신, 미톡산트론, L-아스파라기나제, 독소루비신, 에피루비신, 5-플루오로우라실, 도세탁셀, 파클리탁셀, 류코보린, 레바미솔, 이리노테칸, 에스트라무스틴, 에토포시드, 질소 머스타드, BCNU(bis-chloroethyl nitrosourea; 비스-클로로에틸 니트로소우레아), 카르무스틴, 로무스틴, 빈블라스틴, 빈크리스틴, 비노렐빈, 시스플라틴, 카르보플라틴, 옥살리플라틴, 이마티닙 메실레이트, 아바스틴 (베바시주맙), 헥사메틸멜라민, 토포테칸, 티로신 키나제 억제제, 티르포스틴, 헤르비마이신 A, 제니스테인, 에르브스타틴, 히드록시진, 글라티라머 아세테이트, 인터페론 베타-1a, 인터페론 베타-1b, 나탈리주맙 및 라벤두스틴 A로 이루어진 군으로부터 선택된 제2 화합물; 및 제약상 허용되는 담체를 포함하는,
진행성 신세포 암종, 급성 림프모구성 백혈병, 급성 악성 흑색종, 또는 연조직 또는 골 육종의 치료가 필요한 포유동물에서 상기 진행성 신세포 암종, 급성 림프모구성 백혈병, 급성 악성 흑색종, 또는 연조직 또는 골 육종을 치료하기 위한 제약 조성물.A compound of claim 1; Topoisomerase I inhibitor, mitogen-activated protein extracellular-signal-regulated kinase (MEK) 1/2 inhibitor, heat shock protein 90 (HSP90) Inhibitors, procarbazine, dacarbazine, gemcitabine, capecitabine, methotrexate, taxol, taxotere, mercaptopurine, thioguanine, hydroxyurea, cytarabine, cyclophosphamide, ifosfamide, nitrosourea, Cisplatin, carboplatin, mitomycin, dacarbazine, procarbazine, etoposide, teniposide, camppatin, bleomycin, doxorubicin, idarubicin, daunorubicin, dactinomycin, plicamycin, mitoxane Tron, L-asparaginase, doxorubicin, epirubicin, 5-fluorouracil, docetaxel, paclitaxel, leucovorin, levamisol, irinotecan, esturamustine, etoposide, nitrogen mustard, BCNU (bi s-chloroethyl nitrosourea; bis-chloroethyl nitrosourea), carmustine, lomustine, vinblastine, vincristine, vinorelbine, cisplatin, carboplatin, oxaliplatin, imatinib mesylate, avastin (bevacizumab), Hexamethylmelamine, topotecan, tyrosine kinase inhibitors, tyrphostin, herbimycin A, genistein, ervstatin, hydroxyzine, glatiramer acetate, interferon beta-1a, interferon beta-1b, natalizumab, and rabendu A second compound selected from the group consisting of Stine A; And a pharmaceutically acceptable carrier,
Advanced renal cell carcinoma, acute lymphoblastic leukemia, acute malignant melanoma, or mammalian in need of treatment of soft tissue or osteosarcoma. Pharmaceutical compositions for treating 삭제delete a) 2,4,6-트리클로로[1,3,5]트리아진을
Figure 112012105515194-pct00151
와 반응시켜 중간체 디클로로트리아진 화합물
Figure 112012105515194-pct00152
을 형성하는 단계;
b) 단계 a)로부터의 상기 중간체 디클로로트리아진 화합물을
Figure 112012105515194-pct00153
와 반응시켜 중간체 화합물
Figure 112012105515194-pct00154
을 형성하는 단계;
c) 단계 b)로부터의 상기 중간체를
i) 화학식 R2-B(OH)2의 화합물 또는 그의 에스테르와 반응시켜 화학식 1의 화합물을 수득하는 단계, 또는
ii) 아미노아릴 또는 아미노헤테로아릴 보론산 또는 그의 에스테르와 반응시키고 아미노기를 화학식 I의 우레아로 전환시키는 단계
를 포함하는, 화학식
Figure 112012105515194-pct00155
을 갖는 화합물의 제조 방법
(여기서, R2는 임의로 치환된 C6-C14아릴-NH-COR3, 임의로 치환된 C1-C9헤테로아릴-NH-COR3, -CH=CH-C6-C10아릴-NH-COR3 또는 -CH=CH-C1-C9헤테로아릴-NH-COR3이고;
R3, R4, 및 임의로 치환된 아릴기 및 헤테로아릴기는 제1항에서 정의한 바와 같고;
R6, R7, R8, R9는 각각 독립적으로 수소 원자, 및 C2-C6알케닐, C4-C6알카디에닐, C2-C6알키닐 또는 C4-C6알카디이닐로 임의로 치환된 C1-C6알킬로 이루어진 군으로부터 선택되거나;
또는 R6 및 R7 또는 R8 및 R9 중 하나는, 이들이 부착된 탄소 원자와 함께, O, NH 및 S로부터 독립적으로 선택된 0, 1 또는 2개의 원자를 함유하고, 할로겐, -NH2, -NH(C1-C6알킬), -N(C1-C6알킬)(C1-C6알킬), -N(C1-C3알킬)C(O)(C1-C6알킬), -NHC(O)(C1-C6알킬), -NHC(O)H, -C(O)NH2, -C(O)NH(C1-C6알킬), -C(O)N(C1-C6알킬)(C1-C6알킬), -CN, 히드록실, C1-C6알콕시, C1-C6알킬, -C(O)OH, -C(O)O(C1-C6알킬), -C(O)(C1-C6알킬), C6-C14아릴, C1-C9헤테로아릴 및 C3-C8시클로알킬로 이루어진 군으로부터 선택된 하나 이상의 치환기로 임의로 치환된 5 내지 8원 포화 또는 불포화 고리를 형성한다).a) 2,4,6-trichloro [1,3,5] triazine
Figure 112012105515194-pct00151
Intermediate Dichlorotriazine Compounds by Reaction with
Figure 112012105515194-pct00152
Forming a;
b) the intermediate dichlorotriazine compound from step a)
Figure 112012105515194-pct00153
To react with an intermediate compound
Figure 112012105515194-pct00154
Forming a;
c) removing said intermediate from step b)
i) reacting with a compound of formula R 2 -B (OH) 2 or an ester thereof to obtain a compound of formula 1, or
ii) reacting with aminoaryl or aminoheteroaryl boronic acid or ester thereof and converting the amino group to urea of formula (I)
Formula, including
Figure 112012105515194-pct00155
Method for producing a compound having
Wherein R 2 is optionally substituted C 6 -C 14 aryl-NH-COR 3 , optionally substituted C 1 -C 9 heteroaryl-NH-COR 3 , -CH = CH-C 6 -C 10 aryl-NH -COR 3 or -CH = CH-C 1 -C 9 heteroaryl and -NH-COR 3;
R 3 , R 4 , and optionally substituted aryl groups and heteroaryl groups are as defined in claim 1;
R 6 , R 7 , R 8 , R 9 are each independently a hydrogen atom and C 2 -C 6 alkenyl, C 4 -C 6 alkadienyl, C 2 -C 6 alkynyl or C 4 -C 6 alkadiyi C 1 -C 6 alkyl optionally substituted with niyl;
Or one of R 6 and R 7 or R 8 and R 9 together with the carbon atom to which they are attached contains 0, 1 or 2 atoms independently selected from O, NH and S, halogen, —NH 2 , -NH (C 1 -C 6 alkyl), -N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl), -N (C 1 -C 3 alkyl) C (O) (C 1 -C 6 Alkyl), -NHC (O) (C 1 -C 6 alkyl), -NHC (O) H, -C (O) NH 2 , -C (O) NH (C 1 -C 6 alkyl), -C ( O) N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl), -CN, hydroxyl, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, -C (O) OH, -C ( O) O (C 1 -C 6 alkyl), -C (O) (C 1 -C 6 alkyl), C 6 -C 14 aryl , C 1 -C 9 heteroaryl and C 3 -C 8 cycloalkyl To form a 5-8 membered saturated or unsaturated ring optionally substituted with one or more substituents selected from the group). 제25항에 있어서, 반응 잔기
Figure 112010076169004-pct00156
가
Figure 112010076169004-pct00157
인 방법. The reaction residue of claim 25, wherein the reaction moiety is
Figure 112010076169004-pct00156
end
Figure 112010076169004-pct00157
/ RTI &gt;
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